Cesium carbonate → 4-[3-[6-(3-Benzo[1,3]dioxol-5-yl-5-isobutyryl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester

HRID 417048ノート

反応式

HRID 417048 の反応式
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[CH:11]=[C:12]([C:17](=[O:21])[CH:18]([CH3:20])[CH3:19])[CH:13]=[C:14]([OH:16])[CH:15]=3)=[CH:9][C:4]=2[O:3][CH2:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:28]([O:30][C:31](=[O:56])[CH2:32][CH2:33][CH2:34][O:35][C:36]1[CH:41]=[CH:40][CH:39]=[C:38]([CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47]Br)[C:37]=1[CH2:49][CH2:50][C:51]([O:53][CH2:54][CH3:55])=[O:52])[CH3:29]>CC(C)=O.CN(C=O)C>[CH2:28]([O:30][C:31](=[O:56])[CH2:32][CH2:33][CH2:34][O:35][C:36]1[CH:41]=[CH:40][CH:39]=[C:38]([CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][O:16][C:14]2[CH:13]=[C:12]([C:17](=[O:21])[CH:18]([CH3:19])[CH3:20])[CH:11]=[C:10]([C:8]3[CH:7]=[CH:6][C:5]4[O:1][CH2:2][O:3][C:4]=4[CH:9]=3)[CH:15]=2)[C:37]=1[CH2:49][CH2:50][C:51]([O:53][CH2:54][CH3:55])=[O:52])[CH3:29]

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 575864914-[3-(6-Bromo-hexyl)-2-(ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl esterHCID 594968091-(3-Benzo[1,3]dioxol-5-yl-5-hydroxy-phenyl)-2-methyl-propan-1-one

生成物 1

HCID 594968284-[3-[6-(3-Benzo[1,3]dioxol-5-yl-5-isobutyryl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester収率 75%

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
75 °C

実験手順

To a solution of 1-(3-benzo[1,3]dioxol-5-yl-5-hydroxy-phenyl)-2-methyl-propan-1-one (109 mg) in a mixture of acetone and DMF (2:1, 3 mL) were added cesium carbonate (624 mg) and 4-[3-(6-bromo-hexyl)-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (190 mg). The resulting mixture was stirred at 75° C. overnight. Then the insoluble material was filtered out and the filtrate was diluted with ethyl acetate and washed with water and brine. The organic extract was dried over anhydrous sodium sulfate, concentrated and purified on a silica gel column using ethyl acetate and hexanes to yield 194 mg of the title compound (75% yield). HRMS calcd for C40H50O9 [M+Na]+ 697.3347, observed 697.3344.

後処理

  1. filtrationThen the insoluble material was filtered out
  2. additionthe filtrate was diluted with ethyl acetate
  3. washwashed with water and brine
  4. extractionThe organic extract
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. custompurified on a silica gel column

出典と根拠

ORDレコード
ord-f225f5aa6eb948aaab79b1b46094a556
出典データセット
uspto-grants-2012_01
特許番号
US08088936B2

反応ノート

読み込み中…