1,2-Dimethoxyethane → 4-[2-Benzyloxycarbonyl-2-(4-isobutyl-phenyl)-vinyl]-benzoic acid methyl ester

HRID 2371278ノート

反応式

HRID 2371278 の反応式
[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[C:11]([C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])Br)=[CH:6][CH:5]=1.[CH2:24]([C:28]1[CH:33]=[CH:32][C:31](B(O)O)=[CH:30][CH:29]=1)[CH:25]([CH3:27])[CH3:26].C(=O)([O-])[O-].[Na+].[Na+].C(COC)OC>CC1C=CC=CC=1[P](C1C=CC=CC=1C)([Pd](Cl)(Cl)[P](C1=C(C)C=CC=C1)(C1C=CC=CC=1C)C1C=CC=CC=1C)C1C=CC=CC=1C.O.C(O)C>[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[C:11]([C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[C:31]2[CH:32]=[CH:33][C:28]([CH2:24][CH:25]([CH3:27])[CH3:26])=[CH:29][CH:30]=2)=[CH:6][CH:5]=1

参加物

8

反応物 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 2773472(4-Isobutylphenyl)boronic acidHCID 866697884-(2-Benzyloxycarbonyl-2-bromo-vinyl)-benzoic acid methyl ester

生成物 1

HCID 674864534-[2-Benzyloxycarbonyl-2-(4-isobutyl-phenyl)-vinyl]-benzoic acid methyl ester

試薬・触媒・溶媒 3

HCID 178424406HCID 178424406、化合物触媒HCID 702Ethanol溶媒HCID 962Water溶媒

反応条件

温度
120 °C

実験手順

4-(2-Benzyloxycarbonyl-2-bromo-vinyl)-benzoic acid methyl ester (2.0 g, 5.33 mmol) was added to a 100 mL RB flask containing 4-isobutylphenylboronic acid (2.85 g, 15.99 mmol), sodium carbonate (2.83 g, 26.65 mmol), and dichlorobis(tri-o-tolylphosphine)palladium(II) (544 mg, 0.69 mmol). Dimethoxyethane (16 mL), ethanol (8 mL), and water (4 mL) were added, and the reaction was stirred at 120° C. for 1 hour at which point TLC analysis indicated that the reaction had gone to completion. The reaction was filtered hot through celite and concentrated to dryness. Purification by flash column chromatography was performed on an ISCO Sg-100c system, using a 40 gram pre-packed column and eluting with a linear gradient of ethyl acetate in hexanes starting at 10% EtOAc and ending at 40% EtOAc over 22 minutes. This afforded the desired product, 4-[2-Benzyloxycarbonyl-2-(4-isobutyl-phenyl)-vinyl]-benzoic acid methyl ester as a pale oil, 1.8 g, 79%. LC-MS m/z=429 [C28H28O4+H]+.

後処理

  1. filtrationThe reaction was filtered hot through celite and
  2. concentrationconcentrated to dryness
  3. customPurification by flash column chromatography
  4. washeluting with a linear gradient of ethyl acetate in hexanes starting at 10% EtOAc
  5. waitending at 40% EtOAc over 22 minutes

出典と根拠

ORDレコード
ord-6f09f8fab0cf463d8307dc9e8001a39c
出典データセット
uspto-grants-2014_04
特許番号
US08710236B2

反応ノート

読み込み中…