Sodium borohydride → HCID 10443031, compound

HRID 1914271Notes

Reaction equation

HRID 1914271 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:14])[CH2:11][CH2:12][CH3:13])=[CH:6][CH:5]=1.[BH4-].[Na+]>C(O)C.C1COCC1>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([OH:14])[CH2:11][CH2:12][CH3:13])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 23143286Methyl 4-butyrylbenzoate

Product 1

HCID 10443031HCID 10443031, compoundYield 91.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-butyryl-benzoic acid methyl ester (400 mg, 1.94 mmol) in ethanol (5 mL) and THF (4 mL) is added sodium borohydride (110 mg, 2.9 mmol), the mixture is stirred at room temperature for 2 h. The reaction mixture is quenched by acetic acid (0.5 mL) and water (10 mL), extracted with ethyl acetate. Combined organic layers are washed with brine and dried over sodium sulfate. Concentration and column chromatography on silica gel gives the title compound (370 mg).

Workup

  1. customThe reaction mixture is quenched by acetic acid (0.5 mL) and water (10 mL)
  2. extractionextracted with ethyl acetate
  3. washCombined organic layers are washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationConcentration and column chromatography on silica gel

Sources & evidence

ORD record
ord-255ea8d7b983407c8aa1f7867d8f8870
Source dataset
uspto-grants-2013_12
Patent number
US08609892B2

Reaction notes

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