HRID1464363

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID11430

Potassium Carbonate

CK2O3

结构：[Br-].c1ccc(CCC[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1

HCID10928647

Triphenyl(3-phenylpropyl)phosphanium bromide

C27H26BrP

结构：CC(C)C[C@@H](C(=O)OCc1ccccc1)C(CC=O)(C(=O)OCc1ccccc1)C(=O)OC(C)(C)C

HCID86747779

未命名化合物

PRODUCTS

生成物

结构：CC(C)C[C@@H](C(=O)OCc1ccccc1)C(CC=CCCc1ccccc1)(C(=O)OCc1ccccc1)C(=O)OC(C)(C)C

HCID67826468

未命名化合物

收率 66.4%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID8028

Tetrahydrofuran

C4H8O

PROCEDURE

实验过程

A mixture of 0.496 g of 1,2-dibenzyl 1-tert.butyl 1-(formylmethyl)-4-methyl-1,1,2(R)-pentane tricarboxylate, 0.176 g of potassium carbonate and 0.576 g of 3-phenylpropyltriphenylphosphonium bromide in 8 ml of dry tetrahydrofuran was heated at reflux under a nitrogen atmosphere for 3 days. The solvent was removed by evaporation and stirred with diethyl acetate. The solids which separated were filtered off and the filtrate was evaporated. The residue was purified by flash chromatography on silica gel using hexane/ethyl acetate (6:1) for the elution. There was obtained 0.397 g of 1,2-dibenzyl 1-tert.butyl 4-methyl-1-(5-phenyl-pent-2-en-1-yl)-1,1,2(R)-pentanetricarboxylate in the form of a colorless oil.

WORKUP

后处理

temperaturewas heated
temperatureat reflux under a nitrogen atmosphere for 3 days
customThe solvent was removed by evaporation
customThe solids which separated
filtrationwere filtered off
customthe filtrate was evaporated
customThe residue was purified by flash chromatography on silica gel
washfor the elution

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-5c9379443acd4f52a3f6cb16c13df896
来源数据集: uspto-grants-1994_04
DOI: 10.6084/m9.figshare.5104873.v1
专利: US05304549
来源说明: uspto-grants-1994_04

反应 SMILES

[CH:1]([CH2:3][C:4]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])([C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21])[C@H:5]([C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])[CH2:6][CH:7]([CH3:9])[CH3:8])=O.C(=O)([O-])[O-].[K+].[K+].[Br-].[C:44]1([CH2:50][CH2:51][CH2:52][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>O1CCCC1>[CH3:9][CH:7]([CH3:8])[CH2:6][C@@H:5]([C:10]([O:12][CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:11])[C:4]([CH2:3][CH:1]=[CH:52][CH2:51][CH2:50][C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1)([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21]