Methanol → 3-Thiophenemethanol, 5-(difluoromethyl)-

HRID 2203013Notes

Reaction equation

HRID 2203013 reaction equation
[F:1][CH:2]([F:12])[C:3]1[S:7][CH:6]=[C:5]([C:8](OC)=[O:9])[CH:4]=1.CO.[BH4-].[Na+]>C1COCC1>[F:1][CH:2]([F:12])[C:3]1[S:7][CH:6]=[C:5]([CH2:8][OH:9])[CH:4]=1

Participants

5

Conditions

Temperature
60 °C

Procedure

To a solution of methyl 5-(difluoromethyl)thiophene-3-carboxylate (267 mg) in THF (5 ml)-MeOH (1 ml) was added NaBH4 (263 mg) at room temperature, and the reaction mixture was stirred at 60° C. for 1 h. The reaction mixture was quenched with water, and extracted with EtOAc. The extract was washed with brine, dried over MgSO4, concentrated and purified by silica gel column chromatography (hexane/EtOAc) to give the title compound (192 mg) as a colorless oil.

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with EtOAc
  3. washThe extract was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. custompurified by silica gel column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-d6fdcb311adf40d7ab109ce7274a82da
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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