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US 2014/0235867 A1Published application
Method for producing alpha-hydroxy ketone compound
AssigneeSumitomo Chemical Company, Limited
InventorsKoji Hagiya, Akio Tanaka, Toshihiro Hodai
Life of this patent
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Abstract
The present invention relates to a specific thiazolium salt used for producing an α-hydroxy ketone compound, and a method for producing an α-hydroxy ketone compound by carrying out a coupling reaction of an aldehyde compound in the presence of a base compound and the specific thiazolium salt.
Claims34
A method for producing an α-hydroxy ketone compound by carrying out a coupling reaction of an aldehyde compound in the presence of a base compound and a thiazolium salt defined by a formula (1)
- (wherein R1 and R2 independently denote a hydrogen atom, an alkyl which may have a substituent, an alkoxycarbonyl which may have a substituent, an alkylcarbonyl which may have a substituent, or an aryl which may have a substituent, or R1 and R2 may be bonded to each other to form a ring together with the carbon atoms bonded to R1 and R2;
- R0 denotes a hydrogen atom, a halogen atom, an alkyl which may have a substituent, or an aryl which may have a substituent;
- W0 denotes an aryl which may have a substituent or a halogen atom;
- X− denotes an anion;
- n denotes 1 or 2;
- in the case n is 2, 2 groups denoted by W0 may be mutually the same or different;
- and all or some of a plurality of groups denoted by R0 may be the same or different).
4 more elements
A method for producing an α-hydroxy ketone compound by carrying out a coupling reaction of an aldehyde compound in the presence of thiazol-2-ylidene defined by a formula (1-2)
- (wherein R1 and R2 independently denote a hydrogen atom, an alkyl which may have a substituent, an alkoxycarbonyl which may have a substituent, an alkylcarbonyl which may have a substituent, or an aryl which may have a substituent, or R1 and R2 may be bonded to each other to form a ring together with the carbon atoms bonded to R1 and R2;
- R0 denotes a hydrogen atom, a halogen atom, an alkyl which may have a substituent, or an aryl which may have a substituent;
- W0 denotes an aryl which may have a substituent or a halogen atom;
- n denotes 1 or 2;
- in the case n is 2, 2 groups denoted by W0 may be mutually the same or different;
- and all or some of a plurality of groups denoted by R0 may be the same or different).
3 more elements
A thiazolium salt defined by a formula (1)
- (wherein R1 and R2 independently denote a hydrogen atom, an alkyl which may have a substituent, an alkoxycarbonyl which may have a substituent, an alkylcarbonyl which may have a substituent, or an aryl which may have a substituent, or R1 and R2 may be bonded to each other to form a ring together with the carbon atoms bonded to R1 and R2;
- R0 denotes a hydrogen atom, a halogen atom, an alkyl which may have a substituent, or an aryl which may have a substituent;
- W0 denotes an aryl which may have a substituent or a halogen atom;
- X− denotes an anion;
- n denotes 1 or 2;
- in the case n is 2, 2 groups denoted by W0 may be mutually the same or different;
- and all or some of plurality of groups denoted by R0 may be the same).
4 more elements
A thiazol-2-ylidene defined by a formula (1-2)
- (wherein R1 and R2 independently denote a hydrogen atom, an alkyl which may have a substituent, an alkoxycarbonyl which may have a substituent, an alkylcarbonyl which may have a substituent, or an aryl which may have a substituent, or R1 and R2 may be bonded to each other to form a ring together with the carbon atoms bonded to R1 and R2;
- R0 denotes a hydrogen atom, a halogen atom, an alkyl which may have a substituent, or an aryl which may have a substituent;
- W0 denotes an aryl which may have a substituent or a halogen atom;
- n denotes 1 or 2;
- in the case n is 2, 2 groups denoted by W0 may be mutually the same or different;
- and all or some of a plurality of groups denoted by R0 may be the same).
3 more elements
A method for producing a thiazolium salt defined by a formula (8)
- (wherein R1 and R2 independently denote a hydrogen atom, an alkyl which may have a substituent, an alkoxycarbonyl which may have a substituent, an alkylcarbonyl which may have a substituent, or an aryl which may have a substituent, or R1 and R2 may be bonded to each other to form a ring together with the carbon atoms bonded to R1 and R2;
- R0 denotes a hydrogen atom, a halogen atom, an alkyl which may have a substituent, or an aryl which may have a substituent;
- all or some of 4 groups denoted by R0 may be the same;
- W0′ denotes an aryl which may have a substituent;
- X− denotes an anion;
- and n denotes the same as above) by carrying out a step A of obtaining a 3-(aryl-substituted aryl)-2-thiazole-thione compound defined by a formula (7)
- (wherein R1, R2, R0, W0′, and n respectively denote the same as described above) by a coupling reaction of a 3-(halo-substituted aryl)-2-thiazole-thione compound defined by a formula (6)
- (wherein R1, R2, R0, and X− respectively denote the same as described above;
- and Y0 denotes a halogen atom)
- and an aryl compound defined by a formula (5)
- W0′-L (5)
- (wherein W0′ denotes the same as described above;
- and L denotes a leaving group) in the presence of a palladium catalyst and a step B of oxidizing the 3-(aryl-substituted aryl)-2-thiazole-thione compound defined by the formula (7) and obtained in the step A.
10 more elements
A thiazole-thione compound defined by a formula (7′)
- (wherein R1 and R2 independently denote a hydrogen atom, an alkyl which may have a substituent, an alkoxycarbonyl which may have a substituent, an alkylcarbonyl which may have a substituent, or an aryl which may have a substituent, or R1 and R2 may be bonded to each other to form a ring together with the carbon atoms bonded to R1 and R2;
- R3, R4, and R5 independently denote a hydrogen atom, a halogen atom, an alkyl which may have a substituent, or an aryl which may have a substituent;
- and W1 and W2 independently denote an aryl which may have a substituent or a halogen atom).
Dependencies are inferred from the claim text.