HRID1816492

反应详情

EQUATION

反应方程式

REACTANTS

反应物

结构：COC(=O)CC[C@@H](C)[C@H]1CC=C2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O[Si](C)(C)C(C)(C)C)C(C)(C)[C@@H]1CC3

HCID69410951

未命名化合物

PRODUCTS

生成物

结构：C[C@H](CCC(=O)O)[C@H]1CC=C2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O[Si](C)(C)C(C)(C)C)C(C)(C)[C@@H]1CC3

HCID69410795

未命名化合物

收率 70.8%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID702

Ethanol

C2H6O

溶剂HCID8028

Tetrahydrofuran

C4H8O

溶剂HCID14798

Sodium Hydroxide

HNaO

CONDITIONS

反应条件

温度: 50 °C

PROCEDURE

实验过程

3β-tert-Butyldimethylsilyloxy-4,4-dimethyl-5α-chola-8,14-dien-24-oic acid methyl ester (3.6 g) is dissolved in a mixture of 150 ml of THF, 120 ml of ethanol and 18 ml of 1M sodium hydroxide. The mixture is stirred for 20 hours at room temperature and 2hours at 50° C. After aqueous work-up and crystallisation from ethanol/water, 2.48 g of 3β-tert-butyldimethylsilyloxy-4,4-dimethyl-5α-chola-8,14-dien-24-oic acid is isolated.

WORKUP

后处理

customAfter aqueous work-up and crystallisation from ethanol/water

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-c51324f28b5f43c98d00064417786fa0
来源数据集: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
专利: US06884796B2
来源说明: uspto-grants-2005_04

反应 SMILES

C[O:2][C:3](=[O:37])[CH2:4][CH2:5][C@H:6]([C@@H:8]1[C@:25]2([CH3:26])[C:11]([C:12]3[CH2:13][CH2:14][C@@H:15]4[C@:20]([C:22]=3[CH2:23][CH2:24]2)([CH3:21])[CH2:19][CH2:18][C@H:17]([O:27][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29])[C:16]4([CH3:36])[CH3:35])=[CH:10][CH2:9]1)[CH3:7]>C1COCC1.C(O)C.[OH-].[Na+]>[Si:28]([O:27][C@H:17]1[CH2:18][CH2:19][C@@:20]2([CH3:21])[C@@H:15]([CH2:14][CH2:13][C:12]3[C:11]4[C@:25]([CH3:26])([CH2:24][CH2:23][C:22]=32)[C@@H:8]([C@H:6]([CH3:7])[CH2:5][CH2:4][C:3]([OH:37])=[O:2])[CH2:9][CH:10]=4)[C:16]1([CH3:35])[CH3:36])([C:31]([CH3:34])([CH3:32])[CH3:33])([CH3:30])[CH3:29]