Citric Acid → HCID 23111629, compound

HRID 1181602Notes

Reaction equation

[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[S:14][C:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:12][CH:11]=1)(=[O:3])[CH3:2].[BH4-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(O)C>[OH:3][CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[S:14][C:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:12][CH:11]=1)[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

Ethyl 5-(2-acetylphenyl)thiophene-2-carboxylate (3.52 g) obtained in Step 2 was dissolved in ethanol (30 ml) and the mixture was cooled to 0° C. Sodium borohydride was added and the mixture was stirred overnight at 0° C.—room temperature. The reaction mixture was cooled to 0° C., 10% aqueous citric acid was added dropwise and ethanol was evaporated. The reaction mixture was extracted with ethyl acetate, washed successively with water, saturated aqueous sodium hydrogencarbonate and brine, and dried over sodium sulfate. The organic layer was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1) to give the title compound (3.30 g).

Workup

temperatureThe reaction mixture was cooled to 0° C.
customethanol was evaporated
extractionThe reaction mixture was extracted with ethyl acetate
washwashed successively with water, saturated aqueous sodium hydrogencarbonate and brine
dry with materialdried over sodium sulfate
concentrationThe organic layer was concentrated under reduced pressure
customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record: ord-09ce4c85216b43bc846cba69dfc92d34
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07285572B2

Reaction notes

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