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

HRID 418891

반응식

HRID 418891 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

HCID 53720108HCID 53720108, 화합물수율 99.8%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-3a614e1f23b448ef9a48160ce7b521bf
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093302B2

연결된 노트

불러오는 중…