Reaction equation
[CH2:1]([S:8][CH2:9][C:10]1[CH:14]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=2)[S:12][C:11]=1[C:25](OCC)=[O:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.Cl>O1CCCC1.CCOCC>[CH2:1]([S:8][CH2:9][C:10]1[CH:14]=[C:13]([C:15]2[CH:16]=[CH:17][C:18]([C:21]([F:23])([F:24])[F:22])=[CH:19][CH:20]=2)[S:12][C:11]=1[CH2:25][OH:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of ethyl 3-[(benzylthio)methyl]-5-[4-(trifluoromethyl)phenyl]thiophene-2-carboxylate (intermediate 45, 0.87 g) in dry tetrahydrofuran (5 ml) was cooled to 0° C. and 1M lithium aluminium hydride solution in diethyl, ether (0.299 ml) added. The reaction mixture as stirred with cooling for 3 hours. Water (0.5 ml) was added drop-wise followed by 2M hydrochloric acid (0.5 ml), the further water (50 ml), the resulting mixture was extracted twice with ethyl acetate, the extracts were combined, dried over magnesium sulfate and concentrated. The residue was purified by SPE (Si cartridge) eluting initially with cyclohexane:chloroform (1:1) and then chloroform to give the title compound as a white solid.
Workup
- temperaturewith cooling for 3 hours
- extractionthe further water (50 ml), the resulting mixture was extracted twice with ethyl acetate
- dry with materialdried over magnesium sulfate
- concentrationconcentrated
- customThe residue was purified by SPE (Si cartridge)
- washeluting initially with cyclohexane:chloroform (1:1)
Sources & evidence
- ORD record
- ord-970f584521ce4e678ff7c29f9c38f8c9
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07091237B2
Linked notes
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