1-Ethoxy-4-ethynylbenzene → Tert-butyl 1-(4-((4-ethoxyphenyl)ethynyl)phenyl)ethyl-carbamate

HRID 76170

反応式

HRID 76170 の反応式
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]#[CH:11])=[CH:6][CH:5]=1)[CH3:2].[C:12]([O:16][C:17](=[O:28])[NH:18][CH:19]([C:21]1[CH:26]=[CH:25][C:24](Br)=[CH:23][CH:22]=1)[CH3:20])([CH3:15])([CH3:14])[CH3:13]>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.[Cu]I.C(#N)C>[C:12]([O:16][C:17](=[O:28])[NH:18][CH:19]([C:21]1[CH:22]=[CH:23][C:24]([C:11]#[C:10][C:7]2[CH:8]=[CH:9][C:4]([O:3][CH2:1][CH3:2])=[CH:5][CH:6]=2)=[CH:25][CH:26]=1)[CH3:20])([CH3:13])([CH3:14])[CH3:15]

参加物

6

反応物 2

HCID 27751241-Ethoxy-4-ethynylbenzeneHCID 11983730tert-butyl N-(1-(4-bromophenyl)ethyl)carbamate

生成物 1

HCID 66610473Tert-butyl 1-(4-((4-ethoxyphenyl)ethynyl)phenyl)ethyl-carbamate

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418397HCID 178418397、化合物触媒HCID 6342Acetonitrile溶媒

反応条件

温度
65 °C

実験手順

24.6 g (168 mmol) 1-ethoxy-4-ethynyl-benzene, 52.8 g (176 mmol) [1-(4-Bromo-phenyl)-ethyl]-carbamic acid tert-butyl ester (50.2) and 42.6 mL (307 mmol) TEA are added to 400 mL ACN. The mixture is warmed to 65° C. 8.84 g (7.65 mmol) Pd(PPh3)4 and 2.91 g (15.3 mmol) CuI are added and the reaction mixture is stirred at reflux for 2 h. The mixture is cooled to r.t. and the solvent is removed in vacuo. The crude product is purified by column chromatography (hexane/EtOAC 9:1→3:1).

後処理

  1. temperatureat reflux for 2 h
  2. temperatureThe mixture is cooled to r.t.
  3. customthe solvent is removed in vacuo
  4. customThe crude product is purified by column chromatography (hexane/EtOAC 9:1→3:1)

出典と根拠

ORDレコード
ord-c35eeda1cd3e47fda628a35dcc1b3630
出典データセット
uspto-grants-2014_09
特許番号
US08835472B2

関連ノート

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