三(邻甲基苯基)磷 → Ethyl (E)-4-[2-(5,6-dihydro-5,5-dimethyl-8-(phenylthio)naphthalenyl)ethenyl]benzoate

HRID 1370

反应方程式

HRID 1370 反应方程式
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:8]([CH3:13])([CH3:12])[CH2:7][CH:6]=[C:5]([S:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:4]=2[CH:3]=1.[CH:21]([C:23]1[CH:33]=[CH:32][C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:25][CH:24]=1)=[CH2:22].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C(N(CC)CC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:12][C:8]1([CH3:13])[CH2:7][CH:6]=[C:5]([S:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:4]2[C:3](/[CH:22]=[CH:21]/[C:23]3[CH:33]=[CH:32][C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:25][CH:24]=3)=[CH:2][CH:11]=[CH:10][C:9]1=2

参与物

6

反应物 3

HCID 80271三(邻甲基苯基)磷HCID 108668584-乙烯基-苯甲酸乙基酯HCID 158960184,4-Dimethyl-7-bromo-1-phenylthio-3,4-dihydronaphthalene

产物 1

HCID 19695074Ethyl (E)-4-[2-(5,6-dihydro-5,5-dimethyl-8-(phenylthio)naphthalenyl)ethenyl]benzoate

试剂、催化剂与溶剂 2

HCID 167845palladium acetate催化剂HCID 8471三乙胺溶剂

反应条件

温度
90 °C

实验过程

To a degassed solution of 0.35 g (1.0 mmol) of 2-bromo-5,6-dihydro-5,5-dimethyl-8-(phenylthio)-naphthalene (Compound A35) and 0.34 g (1.9 mmol) of ethyl 4-vinylbenzoate in 4.0 mL of triethylamine, was added 0.066 g (0.2 mmol) of tri-o-tolylphosphine and then 0.025 g (0.1 mmol) of palladium(II) acetate. The reaction was heated at 90° C. for 2.25 h. The reaction was concentrated in vacuo. The residue was purified by flash chromatography (silica, 5% ethyl acetate in hexane), followed by recrystallization using EtOH to afford the title compound as white crystals.

后处理

  1. concentrationThe reaction was concentrated in vacuo
  2. customThe residue was purified by flash chromatography (silica, 5% ethyl acetate in hexane)
  3. customfollowed by recrystallization

来源与证据

ORD记录
ord-6359f090cbac49c6a126e41999e4f8b9
来源数据集
uspto-grants-1998_03
专利号
US05723666

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