HRID1758593

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID3283

Diethyl Ether

C4H10O

HCID24083

Magnesium sulfate anhydrous

MgO4S

$结构：C/C(=C\CBr)CCC[C@H](C)CCC[C@H](C)CCCC(C)C$

HCID12905048

未命名化合物

HCID53906365

6,10,14,18-Tetramethylnonadec-5-en-2-yne

C23H42

PRODUCTS

生成物

$结构：CC1=C(C/C=C(\C)CCCC(C)CCCC(C)CCCC(C)C)C(=O)c2ccccc2C1=O$

HCID5280483

2-methyl-3-[(E)-3,7,11,15-tetramethylhexadec-2-enyl]naphthalene-1,4-dione

C31H46O2

收率 56%

AUXILIARIES

试剂、催化剂与溶剂

催化剂HCID178418778

未命名化合物

结构：COC(c1ccccc1)=[Cr](=C=O)(=C=O)(=C=O)(=C=O)=C=O

催化剂HCID178494494

未命名化合物

溶剂HCID8909

Butyl ether

C8H18O

PROCEDURE

实验过程

A solution of 1 mmol of pentacarbonyl[methoxy(phenyl)carbene]chromium and 1,1 mmol of 6.10.14.18-tetramethyl-5-nonadecen-2-yne from phytyl bromide (isomer ratio E/Z=90/10) in 5 ml of dibutyl ether is heated to 55° C. under nitrogen for 1 hour. After the removal of the solvent, the 1-naphthol-tricarbonyl-chromium complex can be isolated (yield 95%) by chromatography on silica gel at -30° C. with methylene chloride/pentane (2/1), or directly oxidised to the quinone after addition of 10 ml of ether by one-hours stirring with 1,5 mmol of silver (I) oxide in the presence of MgSO4. The obtained mixture is filtered, the solvent removed and the residue purified by chromatography at 10° C. on silica gel with pentane/ether (100/1). There is obtained vitamin K1(20) as a light yellow oil in a total yield of 56%.

WORKUP

后处理

customAfter the removal of the solvent
customthe 1-naphthol-tricarbonyl-chromium complex can be isolated (yield 95%) by chromatography on silica gel at -30° C. with methylene chloride/pentane (2/1)
filtrationThe obtained mixture is filtered
customthe solvent removed
customthe residue purified by chromatography at 10° C. on silica gel with pentane/ether (100/1)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-d2c6156756494daf831862456a824111
来源数据集: uspto-grants-1983_02
DOI: 10.6084/m9.figshare.5104873.v1
专利: US04374290
来源说明: uspto-grants-1983_02

反应 SMILES

[CH3:1][C:2]([CH2:8][CH2:9][CH2:10][CH:11]([CH3:23])[CH2:12][CH2:13][CH2:14][CH:15]([CH3:22])[CH2:16][CH2:17][CH2:18][CH:19]([CH3:21])[CH3:20])=[CH:3][CH2:4][C:5]#[C:6][CH3:7].[CH2:24](Br)/[CH:25]=[C:26](/[CH2:28][CH2:29][CH2:30][C@@H](CCC[C@@H](CCCC(C)C)C)C)\C.CC[O:47][CH2:48][CH3:49].[O-:50]S([O-])(=O)=O.[Mg+2]>C(OCCCC)CCC.C(=[Cr](=C=O)(=C=O)(=C=O)(=C=O)=C(OC)C1C=CC=CC=1)=O.[Ag-]=O>[CH3:7][C:6]1[C:48](=[O:47])[C:49]2[C:25](=[CH:26][CH:28]=[CH:29][CH:30]=2)[C:24](=[O:50])[C:5]=1[CH2:4]/[CH:3]=[C:2](/[CH2:8][CH2:9][CH2:10][CH:11]([CH2:12][CH2:13][CH2:14][CH:15]([CH2:16][CH2:17][CH2:18][CH:19]([CH3:21])[CH3:20])[CH3:22])[CH3:23])\[CH3:1]