Water → HCID 91035131, compound

HRID 2222928Notes

Reaction equation

HRID 2222928 reaction equation
[CH:1]([CH:3]1[CH:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:7]=[C:6]([CH3:14])[CH2:5][CH2:4]1)=[O:2].[BH4-].[Na+].O>CO>[OH:2][CH2:1][CH:3]1[CH:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:7]=[C:6]([CH3:14])[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 91269498HCID 91269498, compound

Product 1

HCID 91035131HCID 91035131, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To ethyl(1R/S,6R/S)-6-formyl-3-methylcyclohex-2-ene-1-carboxylate (516 mg, 2.6 mmol) in methanol (13 mL) at 0° C. was added NaBH4 (199 mg, 5.3 mmol) and the reaction mixture was stirred for 2 h. Water was added, the product extracted with ethyl acetate, and dried over anhydrous sodium sulfate. The solvent was removed in vacuo and the product was purified by flash chromatography over silica gel (ethyl acetate/hexanes, 20/80 to 40/60) to afford ethyl(1R/S,6R/S)-6-(hydroxymethyl)-3-methylcyclohex-2-ene-1-carboxylate.

Workup

  1. extractionthe product extracted with ethyl acetate
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was removed in vacuo
  4. customthe product was purified by flash chromatography over silica gel (ethyl acetate/hexanes, 20/80 to 40/60)

Sources & evidence

ORD record
ord-d92c677142ce42f0aa2b494a93465240
Source dataset
uspto-grants-2008_05
Patent number
US07371747B2

Reaction notes

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