2-(Trimethylsilylmethyl)allyl acetate → Methyl (+-)-trans-4-methylene-2-(3-fluorophenyl)cyclopentanoate

HRID 8776

반응식

HRID 8776 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][CH:13]=1)/[CH:5]=[CH:6]/[C:7]([O:9][CH3:10])=[O:8].C(O[CH2:18][C:19]([CH2:21][Si](C)(C)C)=[CH2:20])(=O)C>C1COCC1.CCCCCC.[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>[CH2:18]=[C:19]1[CH2:21][C@@H:6]([C:7]([O:9][CH3:10])=[O:8])[C@H:5]([C:4]2[CH:11]=[CH:12][CH:13]=[C:2]([F:1])[CH:3]=2)[CH2:20]1

참가 물질

7

반응물 2

HCID 44283472-(Trimethylsilylmethyl)allyl acetateHCID 13415099Methyl (E)-3-fluorocinnamate

생성물 1

HCID 53991082Methyl (+-)-trans-4-methylene-2-(3-fluorophenyl)cyclopentanoate수율 83.9%

시약·촉매·용매 4

HCID 742671,2-Bis(diphenylphosphino)ethane촉매HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

실험 절차

A mixture of methyl trans-3-fluorocinnamate (41.25 g, 229 mmol), tetrakis(triphenylphosphine) palladium(0) (18.5 g, 16 mmol), 1,2-bis(diphenylphosphino)ethane (5.5 g, 13.7 mmol), and 2-((trimethylsilyl)methyl)-2-propen-1-yl acetate (42.66 g, 229 mmol) in THF (300 mL) under nitrogen was heated to reflux for 6 h and then stirred at room temperature for 16 h. The reaction was diluted with hexane and filtered to remove the yellow precipitate. The volatiles were then removed in vacuo and the residue was purified by FC (3 to 5% ethyl acetate in hexanes) to afford the title compound (45 g).

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 6 h
  3. filtrationfiltered
  4. customto remove the yellow precipitate
  5. customThe volatiles were then removed in vacuo
  6. customthe residue was purified by FC (3 to 5% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-7a5cb637174d4ad49a54d0c4b3153ed7
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091211B2

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