Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → HCID 59504500, compound

HRID 418901Notes

Reaction equation

HRID 418901 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]2[CH2:13][CH2:12][CH2:11][C:10]2=O)[CH:6]=[CH:7][CH:8]=1.[C:15]([CH:20]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:17][CH2:18][CH3:19])=[O:16]>>[CH2:18]([O:17][C:15](=[O:16])[CH2:20][C:10]1[CH2:11][CH2:12][CH2:13][C:9]=1[C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)[CH3:19]

Participants

3

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 123629382-(3-Methoxyphenyl)cyclopentan-1-one

Product 1

HCID 59504500HCID 59504500, compoundYield 81.4%

Procedure

Reflux a solution of 2-(3-methoxy-phenyl)-cyclopentanone (4.34 g 22.8 mmoles), and (carboethoxymethylene)-triphenylphosphorane (14.31 g, 41.1 mmoles) in 130 ml of xylenes for 15 hours. Concentrate in vacuo at 40° C. and slurry with ether. Remove triphenyl phosphine oxide by vacuum filtration, and chromatographed on silica with 14% ethyl acetate/hexanes. to yield the 4.83 g of the titled compound. 1H NMR (CDCl3): 7.26 (m, 1H), 6.9 (m, 2H), 6.8 (m, 1H), 4.17 (q, J=7.2, 2H), 3.81 (s, 3H), 3.22 (s, 2H), 2.76 (m, 2H), 2.58 (m, 2H), 1.95 (m, 2H) 1.28 (m, 3H).

Workup

  1. concentrationConcentrate in vacuo at 40° C.
  2. filtrationRemove triphenyl phosphine oxide by vacuum filtration
  3. customchromatographed on silica with 14% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-cf8867497598472a8c18e000bd134a88
Source dataset
uspto-grants-2012_01
Patent number
US08093302B2

Reaction notes

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