Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → HCID 66651947, compound

HRID 418916Notes

Reaction equation

HRID 418916 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]2[CH2:14][C:13]([CH3:16])([CH3:15])[CH2:12][CH2:11][C:10]2=O)[CH:6]=[CH:7][CH:8]=1.[CH3:18][O:19][C:20](=[O:41])[CH:21]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C1(C)C=CC=CC=1.CCOCC>[CH3:18][O:19][C:20](=[O:41])[CH:21]=[C:10]1[CH2:11][CH2:12][C:13]([CH3:16])([CH3:15])[CH2:14][CH:9]1[C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

5

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 59504443HCID 59504443, compound

Product 1

HCID 66651947HCID 66651947, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

Dissolve 2-(3-methoxy-phenyl)-4,4-dimethyl-cyclohexanone (13.1 g, 56.4 mmol) in toluene (135 ml), add (triphenyl-λ5-phosphanylidene)-acetic acid methyl ester (28.3 g, 84.6 mmol. Heat reaction mixture at reflux stirring over night. Dilute with ether, filter and concentrate. Chromatograph on a biotage eluting with 10% ethyl acetate in hexanes to give the title compound (5.3 g 33%): 1H NMR (CDCl3) δ 7.27-7.23(m, 1H), 6.88-6.77 (m, 3H),5.01 (s, 1H), 3.77 (s, 3H), 3.56 (s, 3H), 3.53-3.48 (m, 1H), 2.19-2.10 (m, 1H), 1.78-1.58 (m, 3H), 1.46-1.38 (m, 1H), 1.25-1.20 (m, 1H), 1.11 (s, 3H), 0.96 (s, 3H).

Workup

  1. temperatureHeat
  2. customreaction mixture
  3. temperatureat reflux
  4. filtrationfilter
  5. concentrationconcentrate
  6. washChromatograph on a biotage eluting with 10% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-9be4c1d3979846ec9d308634d19193ef
Source dataset
uspto-grants-2012_01
Patent number
US08093302B2

Reaction notes

Loading…