HRID1658416

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID6585

Peracetic acid

C2H4O3

HCID8857

Ethyl acetate

C4H8O2

结构：CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CCCC[C@]4(C)[C@H]3CC[C@]12C

HCID2723895

5-alpha-Cholestane

C27H48

PRODUCTS

生成物

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

HCID13340606

未命名化合物

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

HCID86733568

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID176

Acetic Acid

C2H4O2

PROCEDURE

实验过程

A solution of 15 g of 3β-acetoxy-5 -cholestane (I) in 250 cc of ethyl acetate was treated with 30 cc peracetic acid (40%) in acetic acid and was irradiated with ultra-violet light of at about 300 mμ wavelength for 24 hours. The resulting reaction mixture was washed consecutively with an aqueous solution of sodium bisulfite, sodium bicarbonate and water and the solvents were evaporated in vacuo to dryness. The residue was chromatographed on a column of silica gel to give 3.5 g of the known 3β-acetoxy-25-hydroxy-5α-cholestane (III), m.p. 125°-126°C and 1.8 g of the known 3β-acetoxy-5α-hydroxy-cholestane (II), m.p. 180°-181°C.

WORKUP

后处理

customwas irradiated with ultra-violet light of at about 300 mμ wavelength for 24 hours
customThe resulting reaction mixture
washwas washed consecutively with an aqueous solution of sodium bisulfite, sodium bicarbonate and water
customthe solvents were evaporated in vacuo to dryness
customThe residue was chromatographed on a column of silica gel

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-6bab6c84f09c4d26a9a6bf3cda518b10
来源数据集: uspto-grants-1976_06
DOI: 10.6084/m9.figshare.5104873.v1
专利: US03963765
来源说明: uspto-grants-1976_06

反应 SMILES

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