Nitromethane → Ethyl 3-(4-methoxyphenyl)-4-nitrobutanoate

HRID 6736

Reaction equation

HRID 6736 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)[CH3:2].CN(C)C(=N)N(C)C.[N+:24]([CH3:27])([O-:26])=[O:25]>>[CH2:1]([O:3][C:4](=[O:15])[CH2:5][CH:6]([C:7]1[CH:8]=[CH:9][C:10]([O:13][CH3:14])=[CH:11][CH:12]=1)[CH2:27][N+:24]([O-:26])=[O:25])[CH3:2]

Participants

4

Reactant 3

HCID 6375NitromethaneHCID 664601,1,3,3-TetramethylguanidineHCID 74728Ethyl 4-methoxycinnamate

Product 1

HCID 23544279Ethyl 3-(4-methoxyphenyl)-4-nitrobutanoate

Procedure

A solution of 3-(4-methoxy-phenyl)acrylic acid ethyl ester (1.0 g) and tetramethyl-guanidine (125 μL) was stirred for 24 h at 70° C. in 2.5 mL nitromethane. The solvent was evaporated and the resulting residue was partitioned in 50 mL 1 N hydrochloric acid and 50 mL ethyl ether. The ethyl ether phase was collected and washed with 50 mL 1 N hydrochloric acid. The ether phase was dried over sodium sulfate and the solvent was evaporated to furnish 1.15 g of 3-(4-methoxyphenyl)-4-nitrobutyric acid ethyl ester.

Workup

  1. customThe solvent was evaporated
  2. customthe resulting residue was partitioned in 50 mL 1 N hydrochloric acid
  3. customThe ethyl ether phase was collected
  4. washwashed with 50 mL 1 N hydrochloric acid
  5. dry with materialThe ether phase was dried over sodium sulfate
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-cf21a2c6a3124730980c313880a02012
Source dataset
uspto-grants-2006_08
Patent number
US07084154B2

Linked notes

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