新戊酰基乙酸甲酯 → 11-[1,1-dimethylethyl]-9-oxo-2,3,6,7-tetrahydro-1H,5H-[1]benzopyrano[6,7,8-ij]quinolizine

HRID 257646笔记

反应方程式

HRID 257646 反应方程式
[CH2:1]1[CH2:14][N:13]2[C:4]3[C:5]([CH2:10][CH2:11][CH2:12]2)=[C:6]([OH:9])[CH:7]=[CH:8][C:3]=3[CH2:2]1.[CH3:15][C:16]([CH3:25])([CH3:24])[C:17](=O)[CH2:18][C:19](OC)=[O:20]>ClCCl>[CH3:15][C:16]([C:17]1[O:9][C:6]2[C:7](=[CH:8][C:3]3[CH2:2][CH2:1][CH2:14][N:13]4[C:4]=3[C:5]=2[CH2:10][CH2:11][CH2:12]4)[C:19](=[O:20])[CH:18]=1)([CH3:25])[CH3:24]

参与物

4

反应物 2

HCID 99597新戊酰基乙酸甲酯2 次HCID 1704748-羟基久洛里定

产物 1

HCID 1978368311-[1,1-dimethylethyl]-9-oxo-2,3,6,7-tetrahydro-1H,5H-[1]benzopyrano[6,7,8-ij]quinolizine收率 71.2%

试剂、催化剂与溶剂 1

HCID 6344二氯甲烷溶剂

实验过程

8-Hydroxyjulolidine (1.0 g, 5.29 mmol) and methyl 4,4-dimethyl-3-oxopentanoate (1.0 g, 6.32 mmol) were heated together under nitrogen at 200° C. for 4 hours, after which time more methyl 4,4-dimethyl-3-oxopentanoate (0.5 g, 3.16 mmol) was added and heating was continued for 2 hours. After cooling to room temperature, the reaction mixture was dissolved in dichloromethane and applied to a short column of silica gel (approx. 200 g). Elution with dichloromethane removed non-polar by-products, while subsequent elution with ether afforded 11-[1,1-dimethylethyl]-9-oxo-2,3,6,7-tetrahydro-1H,5H-[1]benzopyrano[6,7,8-ij]quinolizine (1.12 g, 71% yield) as a brown oil which solidified on standing. The structure of this compound was confirmed by mass spectroscopy and by 1H and 13C NMR spectroscopy.

后处理

  1. temperatureheating
  2. washElution with dichloromethane removed non-polar by-products
  3. washwhile subsequent elution with ether

来源与证据

ORD记录
ord-97536e15d77f4f32a95de4487e5c4281
来源数据集
uspto-grants-1993_11
专利号
US05262549

反应笔记

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