3,4-二甲氧基肉桂酸 → 3,4-Dimethoxycinnamoylchloride

HRID 36923笔记

反应方程式

HRID 36923 反应方程式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[CH:6]=[CH:7][C:8](O)=[O:9].C(Cl)(=O)C([Cl:19])=O>CN(C=O)C.O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[CH:6]=[CH:7][C:8]([Cl:19])=[O:9]

参与物

5

反应物 2

HCID 168483,4-二甲氧基肉桂酸HCID 65578草酰氯

产物 1

HCID 533992063,4-Dimethoxycinnamoylchloride

试剂、催化剂与溶剂 2

HCID 6228N,N-二甲基甲酰胺催化剂HCID 8028四氢呋喃溶剂

实验过程

To a mixture of 3,4-dimethoxycinnamic acid (540 mg), DMF (2 drops) and tetrahydrofuran (10 ml) was added oxalyl chloride (0.27 ml) dropwise. The mixture was stirred at room temperature for 40 minutes, at the end of which time the solvent was distilled off to give 3,4-dimethoxycinnamoyl chloride. The chloride was dissolved in dichloromethane (10 ml) followed by addition of 3-amino-4-(2-methylphenyl)-7,8-dihydrocyclopenta [g] [1]benzopyran-2(6H)-one (582 mg) and N,N-dimethylaniline (0.25 ml). The mixture was then stirred at room temperature for 20 hours, after which it was washed with water, dried (MgSO4) and distilled to remove the solvent. The residue was chromatographed on silica gel and eluted with benzene-acetone (9:1) to give 3-(3,4-dimethoxycinnamoylamino) -4-(2-methylphenyl)-7,8-dihydrocyclopenta[g] 1benzopyran-2(6H)-one as oil. The oil was crystallized from ethanol-isopropyl ether (648 mg, 67.4%). Recrystallization from acetone gave colorless needles, m.p. 159°-160° C.

后处理

  1. distillationwas distilled off

来源与证据

ORD记录
ord-03af43923d334bb58f46283316bba5de
来源数据集
uspto-grants-1995_05
专利号
US05418239

反应笔记

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