tert-Butyl acrylate → Tert-butyl 5-(3-methoxyphenyl)-4-nitrovalerate

HRID 274070Notes

Reaction equation

HRID 274070 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH2:10][N+:11]([O-:13])=[O:12])[CH:4]=1.[C:14]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])(=[O:17])[CH:15]=[CH2:16].N12CCCN=C1CCCCC2>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH:10]([N+:11]([O-:13])=[O:12])[CH2:16][CH2:15][C:14]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 15458tert-Butyl acrylateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 14147965HCID 14147965, compound

Product 1

HCID 20094814Tert-butyl 5-(3-methoxyphenyl)-4-nitrovalerateYield 76.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-methoxy-3-(2-nitroethyl)benzene (22.59 g) and tert-butyl acrylate (15.98 g) in dichloromethane (180 ml) was added a solution of 1,8-diazabicyclo[5.4.0]undec-7-ene (1.90 g) in dichloromethane (45 ml) in an ice bath. After stirring for 18.5 hours at ambient temperature, ice water (70 ml) was added to the solution. The organic layer was separated, washed successively with 1N hydrochloric acid, and brine. The solution was treated with silica gel (70 g) and evaporated in vacuo to give tert-butyl 5-(3-methoxyphenyl)-4-nitrovalerate (29.39 g).

Workup

  1. customThe organic layer was separated
  2. washwashed successively with 1N hydrochloric acid, and brine
  3. additionThe solution was treated with silica gel (70 g)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-4c42e856020f45208d46d1dfde9c6920
Source dataset
uspto-grants-1995_02
Patent number
US05387710

Reaction notes

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