Hydrochloric Acid → HCID 53782394, compound

HRID 1105558Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:25])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[S:12][C:13]([CH:16]=[CH:17][C:18](=[O:24])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:14][CH:15]=1.[BH4-].[Na+].Cl>CO.O>[CH3:1][O:2][C:3](=[O:25])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[S:12][C:13]([CH:16]=[CH:17][CH:18]([OH:24])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:14][CH:15]=1

Participants

Conditions

Temperature: 0 °C

Procedure

1 G of 8-[5-(3-oxooct-1-enyl)thien-2-yl]octanoic acid methyl ester was dissolved in 25 ml of methanol and the solution was cooled to about 0° C. Under vigorous stirring, 0.9 g of sodium borohydride was added and the reaction mixture was warmed slowly to room temperature after a period of 30 minutes. After about 1 hour, the reaction mixture was diluted with water, adjusted to a pH of 5.5 to 6 with dilute hydrochloric acid and extracted with ether. The ether phase was washed with water, dried over sodium sulfate, and then concentrated to dryness under vacuum. The residue was purified by column chromatography (silica gel, using petroleum ether and ethyl acetate as eluants). The product was obtained as 0.9 g of an oil (90% yield); ir (film): 3450 (OH), 1740 (C=O), and 1645 cm-1 (C=C).

Workup

temperaturethe reaction mixture was warmed slowly to room temperature after a period of 30 minutes
extractionextracted with ether
washThe ether phase was washed with water
dry with materialdried over sodium sulfate
concentrationconcentrated to dryness under vacuum
customThe residue was purified by column chromatography (silica gel, using petroleum ether and ethyl acetate as eluants)

Sources & evidence

ORD record: ord-7aaef447111141229cf28ce011d9f05b
Source dataset: uspto-grants-1982_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04309407

Reaction notes

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