Hydrochloric Acid → 1-Nitro-2-phenylethane
Reaction equation
[C:1]1([CH:7]=[CH:8][N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+].Cl>C(Cl)(Cl)Cl.CC(O)C>[C:1]1([CH2:7][CH2:8][N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
2-Phenylnitroethene (5.12 g, 34.3 mmol, from step 15a) was dissolved in CHCl3 /i-PrOH (410:85 mL) and SiO2 (51.4 g) was added. NaBH4 (5.2 g, 137 mmol) was added in portions, and the mixture was stirred for 90 minutes at room temperature. HCl (0.5N, 100, mL) was added, and the mixture was stirred for 30 minutes. The layers were separated, and the aqueous phase was extracted with methylene chloride. The organic layers were combine, dried (MgSO4) and concentrated. The residue was chromatographed on silica gel (eluting with ether:hexanes 1:30) to give the title compound as an oil (3.89 g, 75%).