Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → HCID 53720108, compound

HRID 418891

Reaction equation

HRID 418891 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]2=O)[CH:6]=[CH:7][CH:8]=1.[C:16]([CH:21]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:18][CH2:19][CH3:20])=[O:17]>C1(C)C=CC=CC=1>[CH2:19]([O:18][C:16](=[O:17])[CH:21]=[C:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH:9]1[C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)[CH3:20]

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 858682-(3-Methoxyphenyl)cyclohexanone

Product 1

HCID 53720108HCID 53720108, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Combine 2-(3-methoxyphenyl)-cyclohexanone (5.0 g, 24.5 mmol), carbethoxymethylene triphenylphosphorane (15.4 g, 44.1 mmol), and toluene (150 mL), stir and heat at reflux. After 22 hours, cool to ambient temperature and concentrate under vacuum. Add ether and filter off the triphenylphosphine oxide precipitate and concentrate the ether filtrate. Flash chromatograph with 0% to 10% ethyl acetate/hexanes to yield the titled compound (6.71 g, 99%) as a clear oil. TLC Rf=0.58 in 8:1 hexanes:ethyl acetate. 1H NMR (CDCl3): 7.25 (m, 1H), 6.81-6.79 (m, 3H), 6.73 (s, 1H), 5.14 (s, 1H), 4.07 (q, J=14.4, 7.2, 2H), 3.80 (s, 3H), 3.80-3.69 (m, 1H), 3.39-3.36 (m, 1H), 2.20-2.16 (m, 1H), 2.06-2.03 (m, 1H), 1.96-1.87 (m, 3H), 1.65-1.54 (m, 2H), 1.2 (t, J=1.2, 8, 3H).

Workup

  1. temperatureheat
  2. temperatureat reflux
  3. concentrationconcentrate under vacuum
  4. filtrationAdd ether and filter off the triphenylphosphine oxide precipitate
  5. concentrationconcentrate the ether filtrate

Sources & evidence

ORD record
ord-3a614e1f23b448ef9a48160ce7b521bf
Source dataset
uspto-grants-2012_01
Patent number
US08093302B2

Linked notes

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