Sodium borohydride → 1-(Furan-2-yl)-2-(3-methoxyphenyl)ethan-1-ol

HRID 1803630Notes

Reaction equation

HRID 1803630 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=[O:16])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=1.[BH4-].[Na+]>CO>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]([OH:16])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 610568711-(Furan-2-yl)-2-(3-methoxyphenyl)ethan-1-one

Product 1

HCID 627174681-(Furan-2-yl)-2-(3-methoxyphenyl)ethan-1-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-(Furan-2-yl)-2-(3-methoxyphenyl)ethan-1-one (20 g, 92.56 mmol) was dissolved in MeOH (200 mL), and NaBH4 (3.5 g, 92.52 mmol) was slowly added to the solution at 5° C. After the reaction was completed, the solution was quenched with H2O, and the MeOH was evaporated. The residue was extracted with EtOAc and the organic layer was washed with brine, dried over MgSO4, and evaporated to give the 1-(furan-2-yl)-2-(3-methoxyphenyl)ethan-1-ol as yellow oil: 20 g (crude yield: 98%)

Workup

  1. customthe solution was quenched with H2O
  2. customthe MeOH was evaporated
  3. extractionThe residue was extracted with EtOAc
  4. washthe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. customevaporated

Sources & evidence

ORD record
ord-cfc50fc9df124071abe328827218eeae
Source dataset
uspto-grants-2013_01
Patent number
US08350090B1

Reaction notes

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