Sodium borohydride → 3-(3-Hydroxy-2-propen-1-yl)benzonitrile

HRID 1700283Notes

Reaction equation

HRID 1700283 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=[O:12])[CH:6]=[CH:7][CH:8]=1)#[N:2].[BH4-].[Na+]>CO>[C:1]([C:3]1[CH:4]=[C:5]([CH2:9][CH:10]=[CH:11][OH:12])[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 544772143-Cyano-1-(2-formylethenyl)benzene

Product 1

HCID 700714923-(3-Hydroxy-2-propen-1-yl)benzonitrileYield 72.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To 3-cyano-1-(2-formylethenyl)benzene (1 g) in 30 mL of MeOH were added CeCl3 (1.88 g) and the resulting solution was stirred for 30 minutes and cooled to 0° C. To the solution was then added NaBH4 (0.29 g). The resulting solution was stirred for 1 hour at 0° C. and concentrated. The residue was taken up in 100 mL of saturated aqueous NaHCO3 and extracted with ethyl acetate (3×). The organic layer was dried, concentrated and purified on silica gel column (ethyl acetate/hexane, 1:4) to give 0.73 g of 3-cyano-1-(3-hydroxyprop-2-en-1 yl)benzene.

Workup

  1. stirringThe resulting solution was stirred for 1 hour at 0° C.
  2. concentrationconcentrated
  3. extractionextracted with ethyl acetate (3×)
  4. customThe organic layer was dried
  5. concentrationconcentrated
  6. custompurified on silica gel column (ethyl acetate/hexane, 1:4)

Sources & evidence

ORD record
ord-9c7e51a9140c4f639281f46eee56c149
Source dataset
uspto-grants-2002_02
Patent number
US06350761B1

Reaction notes

Loading…