Sodium borohydride → HCID 71170040, compound

HRID 1803631Notes

Reaction equation

HRID 1803631 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=[O:22])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:9]=1.[BH4-].[Na+]>CO>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]([OH:22])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:9]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 711700351-(Furan-2-yl)-2-(3-benzyloxyphenyl)ethan-1-one

Product 1

HCID 71170040HCID 71170040, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-(Furan-2-yl)-2-(3-benzyloxyphenyl)ethan-1-one (4 kg, 13.69 mol) was dissolved in MeOH (35 L), and NaBH4 (520 g, 13.75 mol) 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-benzyloxyphenyl)ethan-1-ol as yellow oil: 3.97 kg (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-b67e4372c76d47dfb1b43c3c7b854972
Source dataset
uspto-grants-2013_01
Patent number
US08350090B1

Reaction notes

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