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Potassium Carbonate → Methyl 4-[(4E)-5-{2-[(4-tert-butylbenzyl)oxy]phenyl}-3-(4-cyanobenzyl)pent-4-en-1-yl]benzoate

HRID 1672685
ノート
印刷プレビュー

反応式

HRID 1672685 の反応式
[C:1]([C:3]1[CH:31]=[CH:30][C:6]([CH2:7][CH:8](/[CH:21]=[CH:22]/[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[OH:29])[CH2:9][CH2:10][C:11]2[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=2)=[CH:5][CH:4]=1)#[N:2].[C:32]([C:36]1[CH:43]=[CH:42][C:39]([CH2:40]Br)=[CH:38][CH:37]=1)([CH3:35])([CH3:34])[CH3:33].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:32]([C:36]1[CH:37]=[CH:38][C:39]([CH2:40][O:29][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2/[CH:22]=[CH:21]/[CH:8]([CH2:7][C:6]2[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:31][CH:30]=2)[CH2:9][CH2:10][C:11]2[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=2)=[CH:42][CH:43]=1)([CH3:35])([CH3:33])[CH3:34]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 878361-(Bromomethyl)-4-(1,1-dimethylethyl)benzeneHCID 57831354methyl E-4-[3-(4-cyanobenzyl)-5-(2-hydroxyphenyl)pent-4-enyl]benzoate

生成物 1

HCID 57831359Methyl 4-[(4E)-5-{2-[(4-tert-butylbenzyl)oxy]phenyl}-3-(4-cyanobenzyl)pent-4-en-1-yl]benzoate収率 98%

試薬・触媒・溶媒 1

HCID 6342
Acetonitrile
溶媒

実験手順

A solution of 1.4 g (3.13 mmol, 92% pure) of methyl E-4-[3-(4-cyanobenzyl)-5-(2-hydroxyphenyl)pent-4-enyl]benzoate (Example 75A) in 7 ml of dry acetonitrile is mixed with 1.42 g (6.26 mmol) 4-(tert-butyl)benzyl bromide and 1.30 g (9.39 mmol) of anhydrous potassium carbonate and heated to reflux for 12 hours. The mixture is then filtered and the filtrate is concentrated to dryness. The residue is directly purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 10:1, then 1:5). 1.85 g (3.32 mmol, 93% purity, 98% yield) of an oil are isolated.

後処理

  1. temperatureheated
  2. temperatureto reflux for 12 hours
  3. filtrationThe mixture is then filtered
  4. concentrationthe filtrate is concentrated to dryness
  5. customThe residue is directly purified by chromatography on silica gel (mobile phase
  6. custom1.85 g (3.32 mmol, 93% purity, 98% yield) of an oil are isolated

出典と根拠

ORDレコード
ord-772096a8ce0344139d88f8bf0187758d
出典データセット
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07998988B2

反応ノート

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