Ethanol → Methyl 7-(4-butoxyethoxyphenyl)-1-(3-methoxybenzyl)-2,3-dihydro-1-benzazepine-4-carboxylic acid

HRID 586988ノート

反応式

HRID 586988 の反応式
[CH2:1](O)C.Br[C:5]1[CH:6]=[CH:7][C:8]2[N:14]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=3)[CH2:13][CH2:12][C:11]([C:24]([OH:26])=[O:25])=[CH:10][C:9]=2[CH:27]=1.B([O-])([O-])O[C:30]1[CH:35]=[CH:34][C:33]([O:36][CH2:37][CH2:38][O:39][CH2:40][CH2:41][CH2:42][CH3:43])=[CH:32][CH:31]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.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.O>[CH3:1][CH:13]1[CH2:12][C:11]([C:24]([OH:26])=[O:25])=[CH:10][C:9]2[CH:27]=[C:5]([C:30]3[CH:35]=[CH:34][C:33]([O:36][CH2:37][CH2:38][O:39][CH2:40][CH2:41][CH2:42][CH3:43])=[CH:32][CH:31]=3)[CH:6]=[CH:7][C:8]=2[N:14]1[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=1

参加物

8

反応物 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 223289287-Bromo-1-(3-methoxybenzyl)-2,3-dihydro-1-benzazepine-4-carboxylic acidHCID 867568154-Butoxyethoxyphenyl borate

生成物 1

HCID 22329269Methyl 7-(4-butoxyethoxyphenyl)-1-(3-methoxybenzyl)-2,3-dihydro-1-benzazepine-4-carboxylic acid

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒2 回HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

In toluene (15 ml), ethanol (1.5 ml) and water (1.5 ml) were suspended 7-bromo-1-(3-methoxybenzyl)-2,3-dihydro-1-benzazepine-4-carboxylic acid (320 mg), 4-butoxyethoxyphenyl borate (246 mg) and potassium carbonate (285 mg), and the suspension was stirred under argon atmosphere for 30 minutes. Then, to the suspension was added tetrakistriphenylphosphinepalladium (64 mg), and the mixture was heated at 100° C. for 8 hours under argon atmosphere. After allowing to cool, water was added to the mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried with magnesium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was purified with silica gel column chromatography (hexane:ethyl acetate=5:1) to give methyl 7-(4-butoxyethoxyphenyl)-1-(3-methoxybenzyl)-2,3-dihydro-1-benzazepine-4-carboxylic acid (207 mg) as yellow oil.

後処理

  1. temperatureto cool
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried with magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe resulting residue was purified with silica gel column chromatography (hexane:ethyl acetate=5:1)

出典と根拠

ORDレコード
ord-ce58d7828b984b25aa08ae3dc5802745
出典データセット
uspto-grants-2005_08
特許番号
US06936602B1

反応ノート

読み込み中…