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US 2006/0069272 A1Published application
Process for preparing 2,5-disubstituted 3-alkylthiophenes
OwnerGiorgio Bertolini, Marco Frigerioinventors
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Abstract
The present invention relates to a process for preparing 2,5-disubstituted 3-alkyl-thiophenes and more particularly to a process for preparing them that comprises an acylation reaction in position 5 of 2-substituted 3-alkylthiophenes. This process does not need reagents which are difficult to handle and does not need anhydrous conditions or inert atmosphere. The resulting product is obtained in high purity.
Claims27
Process for preparing 2,5-disubstituted 3-alkylthiophenes of formula
- in which
- A represents a CH3, R2CH2, HOCH2 or R2CH(OH)— group,
- B represents a CHOH or CH2 group,
- R1 represents H or a C1-C5 alkyl group,
- R2 represents a C1-C5 alkyl group,
- R3 represents H or a C1-C5 alkyl group or a C1-C5 haloalkyl group, or a halogen chosen from fluorine, chlorine and bromine,
- which comprises:
- (a) reaction of a compound of formula
- in which
- A represents a CHO, CH3, R2CH2 or R2—CO— group, and
- R1 and R2 have the meanings given above;
- with a compound of formula
- in which
- X represents OH, halogen or a group of formula
- or a group of formula
- —OCOOR4 (VI)
- in which
- R4 represents a C1-C5 alkyl, an optionally substituted benzyl or an option-ally substituted aryl, and
- R3 has the meanings given above;
- to give a compound of formula
- in which
- A, R1, R2 and R3 have the meanings given above;
- and
- (b) reduction of the compound of formula IV thus obtained to give the compound of formula I.
21 more elements
Process for preparing 2,3-dimethyl-5-benzylthiophene of formula
- which comprises:
- (a) the reaction of the compound of formula
- with a compound of formula
- in which X represents halogen;
- to give the compound of formula
- (b1) the reduction of compound IVb to give the hydroxylated intermediate compound of formula
- and
- (b2) the reduction of the hydroxylated intermediate compound Ic to give 2,3-dimethyl-5-benzylthiophene (Ia).
5 more elements
Dependencies are inferred from the claim text.