HRID581621

反应详情

EQUATION

反应方程式

REACTANTS

反应物

结构：Cc1ccc(S(=O)(=O)[O-])cc1.c1cc[nH+]cc1

HCID466102

未命名化合物

结构：C=C[C@H](C[C@H](CC#CCOC1CCCCO1)O[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)O[Si](c1ccccc1)(c1ccccc1)C(C)(C)C

HCID57039693

未命名化合物

PRODUCTS

生成物

结构：C=C[C@H](C[C@H](CC#CCO)O[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)O[Si](c1ccccc1)(c1ccccc1)C(C)(C)C

HCID57269476

未命名化合物

收率 86.1%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID887

Methanol

CH4O

PROCEDURE

实验过程

25.16 g (34.4 mmol) of (5S,7S)-2-[5,7-bis-(tert-butyl-diphenylsilanyloxy)-non-8-en-2-ynyloxy]-tetrahydro-pyran was deprotected by treatment at ambient temperature with 1.30 g (15 mol %) of pyridinium p-toluenesulfonate in 290 ml of abs. MeOH. The solution gradually became homogeneous. After 18 h the reaction mixture was quenched by pouring onto crushed ice/Na2CO3, extracted with ether, washed with water, dried over sodium sulfate and evaporated to dryness. Flash chromatography (SiO2, hexane/AcOEt=82/18) yielded 19.17 g of (5S,7S)-5,7-bis-(tert-butyl-diphenyl-silanyloxy)-non-8-en-2-yn-1-ol as yellowish crystals of mp. 114-116°.

WORKUP

后处理

customAfter 18 h the reaction mixture was quenched
additionby pouring
customonto crushed ice/Na2CO3
extractionextracted with ether
washwashed with water
dry with materialdried over sodium sulfate
customevaporated to dryness

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-2e356179f4944994bb876251f73a1d5f
来源数据集: uspto-grants-1999_07
DOI: 10.6084/m9.figshare.5104873.v1
专利: US05919986
来源说明: uspto-grants-1999_07

反应 SMILES

[Si:1]([O:18][C@H:19]([CH2:31][C@H:32]([O:35][Si:36]([C:49]([CH3:52])([CH3:51])[CH3:50])([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[CH:33]=[CH2:34])[CH2:20][C:21]#[C:22][CH2:23][O:24]C1CCCCO1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CO>[C:14]([Si:1]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[O:18][C@H:19]([CH2:31][C@H:32]([O:35][Si:36]([C:49]([CH3:50])([CH3:51])[CH3:52])([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)[CH:33]=[CH2:34])[CH2:20][C:21]#[C:22][CH2:23][OH:24])([CH3:15])([CH3:16])[CH3:17]