HRID65414

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID6344

Dichloromethane

CH2Cl2

HCID11776

Triphenylphosphine

C18H15P

结构：CC(C)(C)[Si](C)(C)O[C@H]1CC[C@]2(C)[C@H]3CC[C@]4(C)C(=O)[C@H]5C[C@H]5[C@H]4[C@@H]3[C@@H](O)[C@H]3O[C@]32C1

HCID13075962

未命名化合物

PRODUCTS

生成物

结构：CC(C)(C)[Si](C)(C)O[C@H]1CC[C@]2(C)[C@H]3CC[C@]4(C)C(=O)[C@H]5C[C@H]5[C@H]4[C@@H]3[C@H](Cl)[C@H]3O[C@]32C1

HCID13075964

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID1049

Pyridine

C5H5N

溶剂HCID5943

Carbon tetrachloride

CCl4

PROCEDURE

实验过程

126 g of 3β-(tert.-butyldimethylsilyloxy)-5,6β-epoxy-7β-hydroxy-15β,16β-methylene-5β-androstan-17-one is dissolved in a mixture of 600 ml of methylene chloride, 600 ml of carbon tetrachloride, and 300 ml of pyridine and stirred with 193.8 g of triphenylphosphine for 2.5 hours. The mixture is then washed with water, dried over sodium sulfate, and concentrated under vacuum. Chromatography on silica gel with hexane-acetone yields 117.4 g of 3β-(tert.-butyldimethylsilyloxy)-7α-chloro-5,6β-epoxy-15β,16β-methylene-5β-androstan-17-one, mp 155.5° C. [α]D =-87° (chloroform).

WORKUP

后处理

washThe mixture is then washed with water
dry with materialdried over sodium sulfate
concentrationconcentrated under vacuum

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-1338a2a8b7d4465a94c1fc263f3ee3bc
来源数据集: uspto-grants-1986_09
DOI: 10.6084/m9.figshare.5104873.v1
专利: US04614616
来源说明: uspto-grants-1986_09

反应 SMILES

[C:1]([Si:5]([CH3:31])([CH3:30])[O:6][C@H:7]1[CH2:24][CH2:23][C@@:22]2([CH3:25])[C@@:9]3([O:29][C@@H:10]3[C@H:11](O)[C@@H:12]3[C@@H:21]2[CH2:20][CH2:19][C@@:17]2([CH3:18])[C@H:13]3[C@@H:14]3[CH2:27][C@@H:15]3[C:16]2=[O:26])[CH2:8]1)([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)[Cl:52]>C(Cl)(Cl)(Cl)Cl.N1C=CC=CC=1>[C:1]([Si:5]([CH3:31])([CH3:30])[O:6][C@H:7]1[CH2:24][CH2:23][C@@:22]2([CH3:25])[C@@:9]3([O:29][C@@H:10]3[C@@H:11]([Cl:52])[C@@H:12]3[C@@H:21]2[CH2:20][CH2:19][C@@:17]2([CH3:18])[C@H:13]3[C@@H:14]3[CH2:27][C@@H:15]3[C:16]2=[O:26])[CH2:8]1)([CH3:4])([CH3:3])[CH3:2]