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

HRID 278279

反応式

HRID 278279 の反応式
[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

参加物

7

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 742671,2-Bis(diphenylphosphino)ethane触媒HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

実験手順

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 rt for 16 h. The reaction was diluted with hexane and filtered to remove 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).

後処理

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

出典と根拠

ORDレコード
ord-2ac026ff5570481492a4fe347a3fdbea
出典データセット
uspto-grants-2002_03
特許番号
US06358979B1

関連ノート

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