Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → HCID 69590831, compound

HRID 984105Notes

Reaction equation

HRID 984105 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=2)[S:5][C:6]=1[CH2:7][S:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[O:15][CH:14](O)[CH2:13][CH2:12]2.[CH3:30][O:31][C:32]([CH:34]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:33]>CCOCC>[CH3:30][O:31][C:32](=[O:33])[CH2:34][CH:14]1[CH:13]=[CH:12][C:11]2[CH:10]=[C:9]([S:8][CH2:7][C:6]3[S:5][C:4]([C:20]4[CH:25]=[CH:24][C:23]([C:26]([F:28])([F:29])[F:27])=[CH:22][CH:21]=4)=[N:3][C:2]=3[CH3:1])[CH:18]=[CH:17][C:16]=2[O:15]1

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 21949478HCID 21949478, compound

Product 1

HCID 69590831HCID 69590831, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
60 °C

Procedure

Mixture of compound 5F (130 mg, 0.3 mmol) and methyl (triphenylphosphoranylidene) acetate (110 mg, 0.33 mmol) in CDCl3 (15 mL) was heated to 60° C. for 2 h. After the reaction mixture was cooled to RT, ether (100 mL) was added and the mixture was passed through a short silica gel column eluted with ether. Solvent was removed to afford compound 5G as an off-white solid (95 mg, 65%). MS: 494 (M+1)+.

Workup

  1. temperatureAfter the reaction mixture was cooled to RT
  2. washeluted with ether
  3. customSolvent was removed

Sources & evidence

ORD record
ord-28aef0c8ad4147dc80f4c8d134a4f940
Source dataset
uspto-grants-2005_03
Patent number
US06867224B2

Reaction notes

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