2-(三甲基硅甲基)烯丙基乙酸酯 → Methyl (+-)-trans-4-methylene-2-(3-fluorophenyl)cyclopentanoate

HRID 8776

反应方程式

HRID 8776 反应方程式
[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

参与物

7

反应物 2

HCID 44283472-(三甲基硅甲基)烯丙基乙酸酯HCID 13415099Methyl (E)-3-fluorocinnamate

产物 1

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

试剂、催化剂与溶剂 4

HCID 742671,2-双(二苯基膦)乙烷催化剂HCID 11979704四三苯基膦钯催化剂HCID 8028四氢呋喃溶剂HCID 8058正己烷溶剂

实验过程

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).

后处理

  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)

来源与证据

ORD记录
ord-7a5cb637174d4ad49a54d0c4b3153ed7
来源数据集
uspto-grants-2006_08
专利号
US07091211B2

关联笔记

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