Sodium borohydride → Methyl thien-2-yl-hydroxyacetate

HRID 1080710Notes

Reaction equation

HRID 1080710 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=[O:11])[C:7]([O:9][CH3:10])=[O:8].[BH4-].[Na+]>C(O)C.O>[OH:11][CH:6]([C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 11217486Methyl alpha-oxo-2-thiopheneacetate

Product 1

HCID 13682356Methyl thien-2-yl-hydroxyacetateYield 88.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of methyl 2-thiopheneglyoxylate (1.01 g) in ethanol (20 ml) in an ice bath was added sodium borohydride (0.113 g) in 1 ml of water, and the mixture was stirred for 10 minutes. The reaction was quenched with aqueous acetic acid and the mixture was partitioned between methylene chloride and water. The organic extract was washed with brine, dried (sodium sulfate) and evaporated to give methyl α-hydroxy-2-thienylacetate as an oil (0.903 g).

Workup

  1. customThe reaction was quenched with aqueous acetic acid
  2. customthe mixture was partitioned between methylene chloride and water
  3. extractionThe organic extract
  4. washwas washed with brine
  5. dry with materialdried (sodium sulfate)
  6. customevaporated

Sources & evidence

ORD record
ord-657ee4f9087f4328a004c25ec7dafb83
Source dataset
uspto-grants-1996_12
Patent number
US05583147

Reaction notes

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