Sodium borohydride → (2-(But-3-en-1-yl)phenyl)methanol

HRID 921198Notes

Reaction equation

HRID 921198 reaction equation
[CH2:1]([C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[CH:7]=[O:8])[CH2:2][CH:3]=[CH2:4].[BH4-].[Na+]>CO>[CH2:1]([C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[CH2:7][OH:8])[CH2:2][CH:3]=[CH2:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 10261375Benzaldehyde, 2-(3-butenyl)-

Product 1

HCID 12063831(2-(But-3-en-1-yl)phenyl)methanolYield 63.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-(but-3-en-1-yl)benzaldehyde (500 mg, 3.12 mmol) in MeOH (10 mL) was added NaBH4(118 mg, 3.12 mmol) and the mixture was stirred at rt for 1 h. It was then added water, extracted with EtOAc. The organic was dried over MgSO4, filtered and concentrated to obtain an oil, which was then purified by biotage, eluting with 10% EtOAc/hexane to obtain (2-(but-3-en-1-yl)phenyl)methanol (320 mg, 1.973 mmol, 63.2% yield) as a clear oil. 1H NMR (400 MHz, CDCl3) δ 7.44-7.37 (m, 1H), 7.33-7.21 (m, 3H), 5.91 (ddt, J=16.9, 10.2, 6.6 Hz, 1H), 5.13-4.99 (m, 2H), 4.76 (d, J=5.9 Hz, 2H), 2.86-2.77 (m, 2H), 2.44-2.35 (m, 2H).

Workup

  1. extractionadded water, extracted with EtOAc
  2. dry with materialThe organic 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-b7d48d2498934d53bac516506986c9b0
Source dataset
uspto-grants-2016_03
Patent number
US09273067B2

Reaction notes

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