Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → HCID 67066687, compound

HRID 1916366Notes

Reaction equation

HRID 1916366 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:4]=1[CH:5]=O.[CH3:14][O:15][C:16]([CH:18]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:17]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:4]=1[CH:5]=[CH:18][C:16]([O:15][CH3:14])=[O:17]

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 27595992-Methoxy-4-nitrobenzaldehyde

Product 1

HCID 67066687HCID 67066687, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-methoxy-4-nitrobenzaldehyde (904 mg, 4.99 mmol) and methyl (triphenylphosphoranylidene) acetate (2.04 g, 5.86 mmol) in CH2Cl2 (25.0 mL) was stirred at 20° C. for 14 h. The solvent was evaporated under reduced pressure and the residue was chromatographed (SiO2 230-400 mesh, 4/1 hexanes/EtOAc) to give the title compound (1.18 g, 4/1 E/Z isomeric mixture, quant.) as a white solid. MS (electrospray, +ions) m/z 238 (M+H).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was chromatographed (SiO2 230-400 mesh, 4/1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-bea889bac2c94f82b8c1144a75adfee9
Source dataset
uspto-grants-2013_12
Patent number
US08618115B2

Reaction notes

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