正己烷 → Tert-butyl {4-[2-(benzyloxy)-2-oxoethyl]phenoxy}acetate

HRID 2225

反应方程式

HRID 2225 反应方程式
[H-].[Na+].CCCCCC.[OH:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])=[CH:12][CH:11]=1.Br[CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30]>CN(C=O)C>[CH2:20]([O:19][C:17]([CH2:16][C:13]1[CH:12]=[CH:11][C:10]([O:9][CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[CH:15][CH:14]=1)=[O:18])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

参与物

6

反应物 4

HCID 8058正己烷HCID 24758氢化钠HCID 79177溴乙酸叔丁酯HCID 111075242-(4-羟苯基)乙酸苄酯

产物 1

HCID 68357704Tert-butyl {4-[2-(benzyloxy)-2-oxoethyl]phenoxy}acetate

试剂、催化剂与溶剂 1

HCID 6228N,N-二甲基甲酰胺溶剂

反应条件

温度
4 °C

实验过程

Sodium hydride (50% w/w dispersion in mineral oil, 2.1 g) was treated under argon with repeated washes of hexane. The oil-free residue was suspended in dry DMF (130 ml) and the product from step (i) (10 g) added in three portions to the cooled (4° C.) stirred mixture. Stirring was continued for a further 15 minutes when tertiary butyl bromoacetate (7.0 ml) was added dropwise over 15 minutes. After 1 hour at 4° C., the mixture was stirred for 6 hours at ambient temperature. The solvent was evaporated in vacuo and the residue partitioned between ethyl acetate and water. The aqueous phase was re-extracted with further ethyl acetate and the combined organic phases washed with water and brine, then dried (MgSO4) and evaporated. The residue, after purification by flash chromatography on silica eluting with dichloromethane, gave tertiary butyl 4-(benzyloxycarbonylmethyl)phenoxyacetate, 7.5 g, as a colourless oil: NMR (CDCl3) d 7.31(5H, m), 7.20(2H, m), 6.85(2H, m), 5.12(2H, s), 4.49(2H, s), 3.60(2H, s), 1.48(9H, s); m/e 356 (M.)+.

后处理

  1. stirringStirring
  2. waitAfter 1 hour at 4° C.
  3. stirringthe mixture was stirred for 6 hours at ambient temperature
  4. customThe solvent was evaporated in vacuo
  5. customthe residue partitioned between ethyl acetate and water
  6. extractionThe aqueous phase was re-extracted with further ethyl acetate
  7. washthe combined organic phases washed with water and brine
  8. dry with materialdried (MgSO4)
  9. customevaporated
  10. customThe residue, after purification by flash chromatography on silica eluting with dichloromethane

来源与证据

ORD记录
ord-747ab4b04253405996f5d607424406f9
来源数据集
uspto-grants-1998_03
专利号
US05728701

关联笔记

加载中…