2-Nitropropane → Methyl 2-(4-chlorophenyl)-4-methyl-4-nitropentanoate

HRID 79543Notes

Reaction equation

HRID 79543 reaction equation
N12CCCN=C1CCCCC2.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=[CH2:24])[C:20]([O:22][CH3:23])=[O:21])=[CH:15][CH:14]=1.[N+:25]([CH:28]([CH3:30])[CH3:29])([O-:27])=[O:26]>CC#N>[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([CH:19]([CH2:24][C:28]([CH3:30])([N+:25]([O-:27])=[O:26])[CH3:29])[C:20]([O:22][CH3:23])=[O:21])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 3982-NitropropaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 11735736Methyl 2-(4-chlorophenyl)acrylate

Product 1

HCID 66617854Methyl 2-(4-chlorophenyl)-4-methyl-4-nitropentanoateYield 98.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1,8-Diazabicyclo[5.4.0]undec-7-ene (33.7 mL, 225.2 mmol) was added to a solution of methyl 2-(4-chlorophenyl)acrylate (36.9 g, 187.7 mmol) and 2-nitropropane (20.2 mL, 225.2 mmol) in CH3CN (500 mL) at 0° C. under nitrogen. The mixture was warmed to room temperature and stirred overnight. The solution was concentrated in vacuo and subjected to column chromatography (20% EtOAc/hexanes) to give methyl 2-(4-chlorophenyl)-4-methyl-4-nitropentanoate (52.9 g, 98.7% yield) as an oil. 1H NMR (CDCl3, 400 MHz) δ 7.31-7.29 (m, 2H), 7.21-7.19 (m, 2H), 3.66 (s, 3H), 3.60-3.57 (m, 1H), 2.87-2.81 (dd, 1H), 2.39-2.34 (dd, 1H), 1.56 (s, 3H), 1.55 (s, 3H).

Workup

  1. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-85d5fe6beab44e11b740863bc7073bb3
Source dataset
uspto-grants-2014_09
Patent number
US08841304B2

Reaction notes

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