Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → HCID 14925556, compound

HRID 1493088Notes

Reaction equation

HRID 1493088 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.[CH3:13][O:14][C:15]([CH:17]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:16]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:9]=[CH:8][C:5](/[CH:6]=[CH:17]/[C:15]([O:14][CH3:13])=[O:16])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 796744-Chloro-2-nitrobenzaldehyde

Product 1

HCID 14925556HCID 14925556, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-Chloro-2-nitrobenzaldehyde (5 g, 0.027M) was dissolved in toluene (150 ml) with methyl (triphenylphosphoranylidene) acetate (9.91 g, 1.1 molar equivalents) and heated under reflux for 1h. The reaction mixture was concentrated under vacuum and the residue was purified by chromatography on silica gel using dichloromethane as eluent to give the required compound (6.4 g, 98%) as a solid. δ(360MHz, CDCl3) 3.83 (3H, s, CH3), 6.36 (1H, d, J=15.9Hz, CHA =CHB), 7.58 (1H, d, J=8.4Hz, 6H), 7.63 (1H, dd, J=8.4 and 2.0Hz, 5-H), 8.04 (1H, d, J=2.0Hz, 3-H), 8.05 (1H, d, J=8.4Hz, CHA =CHB); MS (EI) m/e 241 [M+ ].

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1h
  3. concentrationThe reaction mixture was concentrated under vacuum
  4. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-e2ac4ac6e39748d59ea804cb6164e749
Source dataset
uspto-grants-1994_12
Patent number
US05376748

Reaction notes

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