Ethyl (4-bromo-2,5-dimethyl-thiophen-3-yl)-oxo-acetate → Ethyl 2-(4-bromo-2,5-dimethylthiophen-3-yl)-2-hydroxyacetate

HRID 591053Notes

Reaction equation

HRID 591053 reaction equation
[Br:1][C:2]1[C:3]([C:9](=[O:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:4]([CH3:8])[S:5][C:6]=1[CH3:7].[BH4-].[BH4-].[BH4-].[BH4-].[Na+].[Na+].[Na+].[Na+]>O1CCCC1.C(O)C>[Br:1][C:2]1[C:3]([CH:9]([OH:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:4]([CH3:8])[S:5][C:6]=1[CH3:7]

Participants

5

Reactant 2

HCID 70818387Ethyl (4-bromo-2,5-dimethyl-thiophen-3-yl)-oxo-acetateHCID 131720822Sodium tetraborohydride

Product 1

HCID 70818714Ethyl 2-(4-bromo-2,5-dimethylthiophen-3-yl)-2-hydroxyacetateYield 89%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of ethyl 2-(4-bromo-2,5-dimethylthiophen-3-yl)-2-oxoacetate (28c) (1 g, 3.56 mmol) in tetrahydrofuran (22.5 mL) and ethanol (5.6 mL) cooled to 0° C. is added sodium tetraborohydride (121.2 mg, 3.20 mmol). The mixture is stirred at 0° C. for 1 hour. The mixture is quenched with HCl (1N) and extracted with ethyl acetate. The organic extract is washed with brine, dried over sodium sulfate, filtered and concentrated to afford the desired alcohol (28d) as a white solid (836 mg, 2.85 mmol, 89%) which was used without further purification.

Workup

  1. customThe mixture is quenched with HCl (1N)
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. washis washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f30e2234a6f64b6dbc1c2ebc1f2daa16
Source dataset
uspto-grants-2016_01
Patent number
US09238026B2

Reaction notes

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