Potassium Carbonate → Methyl 4-{(3E)-4-{2-[(4-tert-butylbenzyl)oxy]phenyl}-2-[2-(4-cyanophenyl)ethyl]but-3-en-1-yl}-benzoate

HRID 1913761ノート

反応式

HRID 1913761 の反応式
[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9]Br)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[C:19]([C:21]1[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][CH:29](/[CH:41]=[CH:42]/[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=2[OH:49])[CH2:30][C:31]2[CH:40]=[CH:39][C:34]([C:35]([O:37][CH3:38])=[O:36])=[CH:33][CH:32]=2)=[CH:23][CH:22]=1)#[N:20]>C(#N)C>[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][O:49][C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][C:43]=2/[CH:42]=[CH:41]/[CH:29]([CH2:28][CH2:27][C:24]2[CH:25]=[CH:26][C:21]([C:19]#[N:20])=[CH:22][CH:23]=2)[CH2:30][C:31]2[CH:40]=[CH:39][C:34]([C:35]([O:37][CH3:38])=[O:36])=[CH:33][CH:32]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 878361-(Bromomethyl)-4-(1,1-dimethylethyl)benzeneHCID 57831366Methyl E-4-[2-[2-(4-cyanophenyl)ethyl]-4-(2-hydroxyphenyl)but-3-enyl]benzoate

生成物 1

HCID 57831375Methyl 4-{(3E)-4-{2-[(4-tert-butylbenzyl)oxy]phenyl}-2-[2-(4-cyanophenyl)ethyl]but-3-en-1-yl}-benzoate収率 92%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

2.20 g (9.71 mmol) of 4-(tert-butyl)benzyl bromide and 2.02 g (14.59 mmol) of anhydrous potassium carbonate are added to a solution of 2 g (3.6 mmol) of methyl E4-[2-[2-(4-cyanophenyl)ethyl]-4-(2-hydroxyphenyl)but-3-enyl]benzoate in 8 ml of dry acetonitrile, and the mixture is heated under reflux for 12 hours. The mixture is then filtered and the filtrate is evaporated to dryness. The residue is purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 10:1). 1.9 g (3.30 mmol, 97% purity, 92% yield) of an oil are isolated.

後処理

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 12 hours
  3. filtrationThe mixture is then filtered
  4. customthe filtrate is evaporated to dryness
  5. customThe residue is purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 10:1)
  6. custom1.9 g (3.30 mmol, 97% purity, 92% yield) of an oil are isolated

出典と根拠

ORDレコード
ord-41e1561e5f394cdfaa36435717fd9263
出典データセット
uspto-grants-2013_12
特許番号
US08609727B2

反応ノート

読み込み中…