Sodium borohydride → 2-Buten-1-ol, 4-(phenylmethoxy)-, (E)-

HRID 2255779Notes

Reaction equation

HRID 2255779 reaction equation
[CH2:1]([O:8][CH2:9]/[CH:10]=[CH:11]\[CH:12]=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>C(O)C>[CH2:1]([O:8][CH2:9]/[CH:10]=[CH:11]/[CH2:12][OH:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Conditions

Temperature
0 °C

Procedure

3.9 g of (Z)-4-benzyloxy-2-butenal was dissolved in 60 ml of ethanol, and 850 mg of sodium borohydride was added thereto under stirring at 0° C. The mixture was stirred at 0° C. for 1.5 hours. The reaction solution was poured into ice water and extracted with ethyl acetate. The ethyl acetate solution was washed sequentially with water and with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure, and the residue was subjected to distillation under reduced pressure (2.0 mmHg, 142° C.) to obtain 2.2 g of (E)-4-benzyloxy-2-buten-1-ol as colorless oily substance.

Workup

  1. stirringThe mixture was stirred at 0° C. for 1.5 hours
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate solution was washed sequentially with water and with a saturated sodium chloride aqueous solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThen, the solvent was distilled off under reduced pressure
  6. distillationthe residue was subjected to distillation under reduced pressure (2.0 mmHg, 142° C.)

Sources & evidence

ORD record
ord-1490cff3862a4609b04cb88a0bbc7263
Source dataset
uspto-grants-1993_08
Patent number
US05240924

Reaction notes

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