Sodium borohydride → (1-Methyl-3,4-di(4-benzyloxy-phenyl)-cyclohex-3-enyl)-methanol

HRID 351436Notes

Reaction equation

HRID 351436 reaction equation
[CH3:1][C:2]1([CH:36]=[O:37])[CH2:7][CH2:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:10][CH:9]=2)=[C:4]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:24][CH:23]=2)[CH2:3]1.[BH4-].[Na+]>CO>[CH3:1][C:2]1([CH2:36][OH:37])[CH2:7][CH2:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:10][CH:9]=2)=[C:4]([C:22]2[CH:23]=[CH:24][C:25]([O:28][CH2:29][C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)=[CH:26][CH:27]=2)[CH2:3]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 865958461-Methyl-3,4-di(4-benzyloxy-phenyl)-cyclohex-3-ene carbaldehyde

Product 1

HCID 18436329(1-Methyl-3,4-di(4-benzyloxy-phenyl)-cyclohex-3-enyl)-methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-methyl-3,4-di(4-benzyloxy-phenyl)-cyclohex-3-ene carbaldehyde (200 mg, 0.409 mmol) in MeOH (10.0 mL) at −10° C. was added NaBH4 (100 mg, excess). The reaction mixture was stirred 30 min and then quenched with 51% HCl solution (5 mL), extracted with ethyl acetate (50 mL) and dried over MgSO4. The reaction mixture was then concentrated and purified on SiO2 (50% ethyl acetate/hexane) to yield (1-methyl-3,4-di(4-benzyloxy-phenyl)-cyclohex-3-enyl)-methanol.

Workup

  1. customquenched with 51% HCl solution (5 mL)
  2. extractionextracted with ethyl acetate (50 mL)
  3. dry with materialdried over MgSO4
  4. concentrationThe reaction mixture was then concentrated
  5. custompurified on SiO2 (50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-8b24c97a279343cc8ee11990803fe777
Source dataset
uspto-grants-2007_02
Patent number
US07183445B2

Reaction notes

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