Water → (4-Fluorophenyl)(2-thienyl)methanol

HRID 439831Notes

Reaction equation

HRID 439831 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)=[O:15])=[CH:10][CH:9]=1.O.[OH-].[Na+]>C1COCC1>[F:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)[OH:15])=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 684794-Fluorophenyl 2-thienyl ketoneHCID 21226445Aluminium lithium hydride

Product 1

HCID 10987480(4-Fluorophenyl)(2-thienyl)methanolYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminium hydride (3.68 g, 97 mmol) was added portionwise to a stirred solution of (4-fluorophenyl)-(2-thienyl)ketone (10.0 g, 48.5 mmol) in dry THF (160 ml) at room temperature under argon. The mixture was stirred overnight and water (3.7 ml) added dropwise with caution. After 0.5 h 15% aqueous sodium hydroxide (3.7 ml) was added and the mixture stirred for 0.5 h, finally water (11 ml) was added and the mixture stirred for 0.5 h. The precipitate was removed by filtration through celite and the flitrate was concentrated under reduced pressure to give (4-fluorophenyl)-(2-thienyl)methanol (10.0 g, 99%) as a yellow oil.

Workup

  1. stirringthe mixture stirred for 0.5 h
  2. stirringthe mixture stirred for 0.5 h
  3. customThe precipitate was removed by filtration through celite
  4. concentrationthe flitrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f1789b4911b546f191c323347b3f4f65
Source dataset
uspto-grants-1996_05
Patent number
US05516783

Reaction notes

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