Sodium borohydride → (3-(But-3-en-1-yl)phenyl)methanol

HRID 921209Notes

Reaction equation

HRID 921209 reaction equation
[CH2:1]([C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)[CH:8]=[O:9])[CH2:2][CH:3]=[CH2:4].[BH4-].[Na+]>CO>[CH2:1]([C:5]1[CH:6]=[C:7]([CH2:8][OH:9])[CH:10]=[CH:11][CH:12]=1)[CH2:2][CH:3]=[CH2:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 109208153-(But-3-en-1-yl)benzaldehyde

Product 1

HCID 68725274(3-(But-3-en-1-yl)phenyl)methanolYield 55%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3-(but-3-en-1-yl)benzaldehyde (300 mg, 1.873 mmol) in MeOH (5 mL) was added sodium borohydride (142 mg, 3.75 mmol) and the mixture was stirred at rt for 1 h. It was then added water, extracted with EtOAc. The organic layer was dried over MgSO4, filtered and concentrated to obtain an oil, which was then purified by biotage, eluting with 10% EtOAc/hexane to obtain (3-(but-3-en-1-yl)phenyl)methanol (167 mg, 1.029 mmol, 55.0% yield) as an oil. 1H NMR (400 MHz, CDCl3) δ 7.45-7.10 (m, 4H), 5.88 (ddt, J=17.0, 10.4, 6.5 Hz, 1H), 5.15-4.94 (m, 2H), 4.70 (br. s., 2H), 2.84-2.71 (m, 2H), 2.48-2.34 (m, 2H).

Workup

  1. extractionadded water, extracted with EtOAc
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto obtain an oil, which
  6. customwas then purified by biotage
  7. washeluting with 10% EtOAc/hexane

Sources & evidence

ORD record
ord-a019114b9e144d1c948cca05492c7430
Source dataset
uspto-grants-2016_03
Patent number
US09273067B2

Reaction notes

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