Water → HCID 19392066, compound

HRID 1755981Notes

Reaction equation

HRID 1755981 reaction equation
[BH4-].[Na+].[O:3]=[C:4]1[CH2:9][CH2:8][C:7]2([CH3:10])[C:5]1([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:6]2.O>C(O)C>[OH:3][CH:4]1[CH2:9][CH2:8][C:7]2([CH3:10])[C:5]1([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:6]2

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 14782968HCID 14782968, compound

Product 1

HCID 19392066HCID 19392066, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.4 g (0.01 mol) of sodium borohydride is added at room temperature to 1.8 g (0.01 mol) of ethyl 2-keto-5-methyl-bicyclo[3.1.0]hexane-1-carboxylate, dissolved in 20 ml of ethanol, and the mixture is then subsequently stirred at room temperature for about 12 hours. The reaction mixture is poured into water. The residue is extracted with diethyl ether, concentration is effected, and the crude product is chromatographed on silica gel with hexane/ethyl acetate as eluent. 1.5 g (82% of theory ) of ethyl 2-hydroxy-5-methyl-bicyclo[3.1.0]hexane-1-carboxylate are obtained in the form of an oil.

Workup

  1. extractionThe residue is extracted with diethyl ether, concentration
  2. customthe crude product is chromatographed on silica gel with hexane/ethyl acetate as eluent

Sources & evidence

ORD record
ord-a7c6e47ff36d43839de537c6b5b78a98
Source dataset
uspto-grants-1995_08
Patent number
US05439874

Reaction notes

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