Sulfuric Acid → 2-(4-Fluorophenyl)-5-(2-hydroxyethyl)-3-[4-(methylsulfonyl)phenyl]thiophene

HRID 1899086Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([CH2:13][C:14](OC)=[O:15])=[CH:10][C:9]=2[C:18]2[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][CH:19]=2)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.S(=O)(=O)(O)O>C(OCC)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:12][C:11]([CH2:13][CH2:14][OH:15])=[CH:10][C:9]=2[C:18]2[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:25])=[O:26])=[CH:20][CH:19]=2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of methyl 5-(4-fluorophenyl)-4-[4-(methylsulfonyl)phenyl]thiophene-2-acetate (1.8 g) and lithium aluminum hydride (0.63 g) in diethyl ether (30 ml) was stirred at 0° C. for 1 hour. Ethyl acetate and 10% sulfuric acid (50 ml) were added, and the resulting mixture was filtered. The organic layer was separated, washed with water, dried and concentrated under reduced pressure. The residual pale yellow oil (1.6 g) was purified by column chromatography on silica gel eluting with a mixture of toluene and ethyl acetate (2:1). The obtained oil (1.4 g) was pulverized with hexane to give a yellow powder of 2-(4-fluorophenyl)-5-(2-hydroxyethyl)-3-[4-(methylsulfonyl)phenyl]thiophene.

Workup

filtrationthe resulting mixture was filtered
customThe organic layer was separated
washwashed with water
customdried
concentrationconcentrated under reduced pressure
customThe residual pale yellow oil (1.6 g) was purified by column chromatography on silica gel eluting with a mixture of toluene and ethyl acetate (2:1)

Sources & evidence

ORD record: ord-44239d0051d34d449c0712c761791bb8
Source dataset: uspto-grants-1996_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05571810

Reaction notes

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