Water → tert-Butyl 2-[3-(Allyloxycarbonylmethyl)phenoxy]-2-methylpropionate

HRID 480686ノート

反応式

HRID 480686 の反応式
[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH2:12][CH:13]=[CH2:14])=[O:10])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Br[C:22]([CH3:31])([CH3:30])[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24].O>CN(C)C=O>[CH2:12]([O:11][C:9]([CH2:8][C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=1)[O:1][C:22]([CH3:31])([CH3:30])[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[O:10])[CH:13]=[CH2:14]

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 90290tert-Butyl 2-bromo-2-methylpropionateHCID 18766560Allyl 3-hydroxyphenylacetate

生成物 1

HCID 18766493tert-Butyl 2-[3-(Allyloxycarbonylmethyl)phenoxy]-2-methylpropionate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

Allyl 3-hydroxyphenylacetate (2.64 g, 13.7 mmol), potassium carbonate (3.79 g, 27.4 mmol), and tert-butyl 2-bromoisobutyrate (7.65 g, 34.3 mmol) were dissolved in dimethylformamide (5 mL), and the mixture was stirred for 13 hours at 80° C. The reaction mixture was added to water, and the resultant mixture was extracted with diethyl ether. Washing was performed sequentially with water and saturated brine, followed by drying over magnesium sulfate. The mixture was subjected to concentration under reduced pressure and purification by silica gel column chromatography (n-hexane/ethyl acetate=20/1), whereby the target compound was obtained (3.47 g, 10.38 mmol, 75.7%).

後処理

  1. extractionthe resultant mixture was extracted with diethyl ether
  2. washWashing
  3. dry with materialby drying over magnesium sulfate
  4. concentrationThe mixture was subjected to concentration under reduced pressure and purification by silica gel column chromatography (n-hexane/ethyl acetate=20/1), whereby the target compound
  5. customwas obtained (3.47 g, 10.38 mmol, 75.7%)

出典と根拠

ORDレコード
ord-e4bb55fcf7314091838a119632fd7785
出典データセット
uspto-grants-2003_11
特許番号
US06653334B1

反応ノート

読み込み中…