Methyl Cinnamate → Methyl 4-methylene-2-phenylcyclopentanecarboxylate, trans-

HRID 993206

반응식

HRID 993206 반응식
[C:1]([O:11][CH3:12])(=[O:10])/[CH:2]=[CH:3]/[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(O[CH2:17][C:18]([CH2:20][Si](C)(C)C)=[CH2:19])(=O)C>C1COCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)CCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:17]=[C:18]1[CH2:20][C@@H:2]([C:1]([O:11][CH3:12])=[O:10])[C@H:3]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:19]1

참가 물질

6

반응물 2

HCID 637520Methyl CinnamateHCID 44283472-(Trimethylsilylmethyl)allyl acetate2회

생성물 1

HCID 12537224Methyl 4-methylene-2-phenylcyclopentanecarboxylate, trans-수율 92.5%

시약·촉매·용매 3

HCID 742671,2-Bis(diphenylphosphino)ethane촉매HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of methyl trans-cinnamate (5.0 g, 31 mmol), tetrakis(triphenylphosphine) palladium(0) (2.6 g, 2.3 mmol), 1,2-bis(diphenylphosphino)ethane (0.70 g, 1.8 mmol) and 2-((trimethylsilyl)methyl)-2-propen-1-yl acetate (6.90 g, 37 mmol) in THF (60 mL) under argon was heated to reflux for 4 h. An additional aliquot of 2-((trimethylsilyl)methyl)-2-propen-1-yl acetate (3.40 g) was added and the reaction was continued for another 16 h. The volatiles were then removed in vacuo and the residue was purified by FC (10% ethyl acetate in hexanes) to afford the title compound (6.2 g).

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 4 h
  3. customThe volatiles were then removed in vacuo
  4. customthe residue was purified by FC (10% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-79e976a22e304948b843938dd12dbcf3
출처 데이터셋
uspto-grants-2002_10
특허 번호
US06472410B1

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