Acetic Acid → 2-(4-Fluorophenyl)-5-(1-hydroxyethyl)-3-[4-(methylsulfonyl)phenyl]thiophene

HRID 1899084Notes

Reaction equation

HRID 1899084 reaction equation
[C:1]([C:4]1[S:8][C:7]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)=[C:6]([C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=2)[CH:5]=1)(=[O:3])[CH3:2].[BH4-].[Na+].C(O)(=O)C>CO>[F:15][C:12]1[CH:11]=[CH:10][C:9]([C:7]2[S:8][C:4]([CH:1]([OH:3])[CH3:2])=[CH:5][C:6]=2[C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:23])=[O:24])=[CH:18][CH:17]=2)=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 106431405-Acetyl-2-(4-fluorophenyl)-3-[4-(methylsulfonyl)phenyl]thiophene

Product 1

HCID 233726602-(4-Fluorophenyl)-5-(1-hydroxyethyl)-3-[4-(methylsulfonyl)phenyl]thiopheneYield 73.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 5-acetyl-2-(4-fluorophenyl)-3-[4-(methylsulfonyl)phenyl]thiophene (1 g) and sodium borohydride (0.12 g) in methanol (19 ml) was stirred at ambient temperature for 2 hours. Acetic acid (1 ml) was added and the mixture was concentrated. The residue was dissolved in ethyl acetate, washed with water and an aqueous solution of sodium bicarbonate, dried and concentrated. The residue was recrystallized from a mixture of hexane and ethyl acetate to give crystals of 2-(4-fluorophenyl)-5-(1-hydroxyethyl)-3-[4-(methylsulfonyl)phenyl]thiophene (0.74 g).

Workup

  1. concentrationthe mixture was concentrated
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with water
  4. dry with materialan aqueous solution of sodium bicarbonate, dried
  5. concentrationconcentrated
  6. customThe residue was recrystallized from a mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-576979ee323449379c6526d3a7254f94
Source dataset
uspto-grants-1996_11
Patent number
US05571810

Reaction notes

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