Lithium borohydride → 2-Benzyloxy-4-hydroxymethyl-benzonitrile
Reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([C:10]#[N:11])=[C:6]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:5]=1.[Li+].[BH4-]>C1COCC1>[CH2:13]([O:12][C:6]1[CH:5]=[C:4]([CH2:3][OH:2])[CH:9]=[CH:8][C:7]=1[C:10]#[N:11])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
3-Benzyloxy-4-cyano-benzoic acid methyl ester from step 1 (400 mg, 1.5 mmol ) was dissolved in THF (7.5 ml). LiBH4 in THF (2 M, 1.5 ml, 3 mmol) was added. The reaction mixture was heated at 70° C. for 3 hours. The reaction was quenched carefully with 3N HCl and then extracted with EtOAc (3×10 mL). The organic layers were combined, washed with brine, dried (MgSO4), filtered and concentrated to yield the desired product.