Process for producing retinol and intermediate compounds for producing the same
AssigneeSumitomo Chemical Company, Limited
InventorsToshiya Takahashi, Shinzo Seko, Kazutaka Kimura, Noriyuki Doi, Naoto Konya
Life of this patent
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Abstract
There are disclosed a disulfone compound of formula (1): wherein Ar denotes an aryl group that may have a substituent, R1 denotes a hydrogen atom or a protective group of a hydroxyl group and the wavy line means that the disulfone compound is an E or Z geometrical isomer or a mixture thereof, a method for producing the same, intermediate compounds therefore and a process for producing retinol through the disulfone compound.
Claims30
A disulfone compound of formula (1):
- wherein Ar denotes a substituted or unsubstituted aryl group, R1 denotes a hydrogen atom or a protective group of a hydroxyl group and the wavy line means that the disulfone compound is an E or Z geometrical isomer or a mixture thereof.
A process for producing a disulfone compound of formula (1):
- wherein Ar denotes a substituted or unsubstituted aryl group, R1 denotes a hydrogen atom or a protective group of a hydroxyl group and the wavy line means that the disulfone compound is an E or Z geometrical isomer or a mixture thereof, which comprises reacting an allylsulfone of formula (2):
- wherein Ar and the wavy line have the same meanings as defined in connection with formula (1) above, with an allyl halide compound of formula (3):
- wherein X denotes a halogen atom, R denotes a protective group of a hydroxyl group and the wavy line has the same meanings as defined above, in the presence of a base selected from an alkyl lithium, an alkali metal alkoxide, an alkali metal amide, an alkali metal hydride, or an alkali metal hydroxide.
A process for producing Retinol, which comprises reacting a disulfone compound of formula (1):
- wherein Ar denotes an aryl group that may have a substituent, R1 denotes a hydrogen atom or a protective group of a hydroxyl group and the wavy line means that the disulfone compound is an E or Z geometrical isomer or a mixture thereof, with a base selected from an alkali metal hydroxide, an alkali metal hydride, an alkali metal alkoxide or an alkali metal amide, and optionally deprotecting.
An allylsulfone compound of formula (2):
- wherein Ar denotes a substituted or unsubstituted aryl group and the wavy line means that the allylsulfone compound is an E or Z geometrical isomer or a mixture thereof.
A process for producing an allylsulfone compound of formula (2):
- wherein Ar denotes a substituted or unsubstituted aryl group and the wavy line means that the allylsulfone compound is an E or Z geometrical isomer or a mixture thereof, which comprises reacting, in the presence of a palladium catalyst, a sulfone compound of formula (4):
- wherein R denotes a protective group of a hydroxyl group, and Ar and the wavy line have the same meanings as defined above, with an arylsulfinate of formula (5):
- ArSO2M (5)
- wherein Ar has the same meaning as defined above and M denotes an alkali metal.
A process for producing a sulfone of formula (4):
- wherein R denotes a protective group of a hydroxyl group, and Ar denotes a substituted or unsubstituted aryl group, R denotes a protective group of a hydroxy group, and the wavy line means that the sulfone compound is an E or Z geometrical isomer or a mixture thereof, which comprises reacting a sulfone of formula (6):
- wherein Ar has the same meaning as defined above, with an allyl halide compound of formula (3):
- wherein X denotes a halogen atom, and R and the wavy line have the same meanings as defined above, in the presence of a base selected from an alkyl lithium, an alkali metal alkoxide, an alkali metal amide, or an alkali metal hydride.
Dependencies are inferred from the claim text.