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Sodium Carbonate → 3-{6-[2-(2-Ethoxycarbonyl-ethyl)-3-(3-ethoxycarbonyl-propoxy)-phenyl]-hexyloxy}-5-(4-methyl-thiophen-3-yl)-benzoic Acid tert-butyl Ester

HRID 1670097
ノート
印刷プレビュー

反応式

HRID 1670097 の反応式
[C:1]([O:5][C:6](=[O:43])[C:7]1[CH:12]=[C:11]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH2:27][CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[C:21]=2[CH2:35][CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])[CH:10]=[C:9](Br)[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].[CH3:50][C:51]1[C:52](B(O)O)=[CH:53][S:54][CH:55]=1>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([O:5][C:6](=[O:43])[C:7]1[CH:8]=[C:9]([C:52]2[C:51]([CH3:50])=[CH:55][S:54][CH:53]=2)[CH:10]=[C:11]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH2:27][CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[C:21]=2[CH2:35][CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])[CH:12]=1)([CH3:4])([CH3:3])[CH3:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 50839314-Methyl-3-thiopheneboronic acidHCID 673397313-Bromo-5-{6-[2-(2-ethoxycarbonyl-ethyl)-3-(3-ethoxycarbonyl-propoxy)-phenyl]-hexyloxy}-benzoic Acid tert-butyl Ester

生成物 1

HCID 673389343-{6-[2-(2-Ethoxycarbonyl-ethyl)-3-(3-ethoxycarbonyl-propoxy)-phenyl]-hexyloxy}-5-(4-methyl-thiophen-3-yl)-benzoic Acid tert-butyl Ester収率 88%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒
HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
85 °C

実験手順

3-Bromo-5-{6-[2-(2-ethoxycarbonyl-ethyl)-3-(3-ethoxycarbonyl-propoxy)-phenyl]-hexyloxy}-benzoic acid tert-butyl ester (2.0 g) was dissolved in 1,2-dimethoxyethane (40 mL), followed by addition of Pd(PPh3)4 (80 mg), 2 M solution of sodium carbonate (6 mL) and 4-methyl-3-thiopheneboronic acid (641 mg). The resulting reaction mixture was stirred at 85° C. for 2 h. After cooling the reaction mixture was filtered through Celite™, diluted with ethyl acetate and washed with water and brine. The organic extract was dried over anhydrous sodium sulfate, concentrated under reduced pressure and purified on a silica gel column using ethyl acetate and hexanes to the title compound (1.8 g, 88% yield).

後処理

  1. customThe resulting reaction mixture
  2. temperatureAfter cooling the reaction mixture
  3. filtrationwas filtered through Celite™
  4. additiondiluted with ethyl acetate
  5. washwashed with water and brine
  6. extractionThe organic extract
  7. dry with materialwas dried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. custompurified on a silica gel column

出典と根拠

ORDレコード
ord-0e5b2314766048819fb39bdf3b9e406e
出典データセット
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07989454B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート