Tetrahydrofuran → (2-Fluoro-5-methylphenyl)methanol

HRID 1066806Notes

Reaction equation

HRID 1066806 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:3]=1[CH:4]=[O:5].O1CCCC1.[BH4-].[Na+]>CO>[F:1][C:2]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:3]=1[CH2:4][OH:5]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 32778232-Fluoro-5-methylbenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 12407611(2-Fluoro-5-methylphenyl)methanolYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-fluoro-5-methylbenzaldeyde (1.80 g, 12.3 mmol) in 3:1 tetrahydrofuran:methanol (82 ml total) at 0° C. was treated with sodium borohydride (0.93 g, 24.6 mmol). The reaction was slowly warmed to ambient temperature and stirred for about three hours. The reaction was quenched with water, transferred to a separatory funnel, and extracted with methylene chloride. The organic fraction was dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was further purified by high performance liquid chromatography to yield 1.3 grams (76%) of a clear oil.

Workup

  1. customThe reaction was quenched with water
  2. customtransferred to a separatory funnel
  3. extractionextracted with methylene chloride
  4. dry with materialThe organic fraction was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was further purified by high performance liquid chromatography

Sources & evidence

ORD record
ord-e8f803bc205341ada4e7d81e74a070fd
Source dataset
uspto-grants-2001_06
Patent number
US06245761B1

Reaction notes

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