1,4-Dibromobutane → Methyl 4-[(4E)-5-[2-(4-bromobutoxy)phenyl]-3-(4-cyanobenzyl)pent-4-en-1-yl]benzoate

HRID 1913797ノート

反応式

HRID 1913797 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].[Br:32][CH2:33][CH2:34][CH2:35][CH2:36]Br.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:32][CH2:33][CH2:34][CH2:35][CH2:36][O:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1/[CH:22]=[CH:21]/[CH:8]([CH2:7][C:6]1[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:31][CH:30]=1)[CH2:9][CH2:10][C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=1

参加物

5

反応物 3

HCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 57831354methyl E-4-[3-(4-cyanobenzyl)-5-(2-hydroxyphenyl)pent-4-enyl]benzoate

生成物 1

HCID 59180489Methyl 4-[(4E)-5-[2-(4-bromobutoxy)phenyl]-3-(4-cyanobenzyl)pent-4-en-1-yl]benzoate

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A solution of 664 mg (1.62 mmol) of methyl E-4-[3-(4-cyanobenzyl)-5-(2-hydroxyphenyl)pent-4-enyl]benzoate (enantiomer 1, Example 51A) in 28 ml of dry acetonitrile is mixed with 1743 mg (8.07 mmol) of 1,4-dibromobutane and 446 mg (3.23 mmol) of anhydrous potassium carbonate and then heated under reflux for 12 h. The mixture is subsequently filtered, and the filtrate is evaporated to dryness. The residue is purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 10:1). 790 mg (1.44 mmol, 89% of theory) of a colourless oil are isolated.

後処理

  1. temperatureheated
  2. temperatureunder reflux for 12 h
  3. filtrationThe mixture is subsequently 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. custom790 mg (1.44 mmol, 89% of theory) of a colourless oil are isolated

出典と根拠

ORDレコード
ord-ef7dd875e5044d2ba0688d02141c0ad8
出典データセット
uspto-grants-2013_12
特許番号
US08609727B2

反応ノート

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