Potassium Carbonate → Ethyl E-8-[2-(4-tert-butylbenzyloxy)phenyl]-6-(4-cyanobenzyl)oct-7-enoate

HRID 1927444ノート

反応式

HRID 1927444 の反応式
[C:1]([C:3]1[CH:28]=[CH:27][C:6]([CH2:7][CH:8](/[CH:18]=[CH:19]/[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[OH:26])[CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:5][CH:4]=1)#[N:2].[C:29]([C:33]1[CH:40]=[CH:39][C:36]([CH2:37]Br)=[CH:35][CH:34]=1)([CH3:32])([CH3:31])[CH3:30].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:29]([C:33]1[CH:34]=[CH:35][C:36]([CH2:37][O:26][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2/[CH:19]=[CH:18]/[CH:8]([CH2:7][C:6]2[CH:27]=[CH:28][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)[CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:39][CH:40]=1)([CH3:32])([CH3:30])[CH3:31]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 878361-(Bromomethyl)-4-(1,1-dimethylethyl)benzeneHCID 57831344Ethyl E-6-(4-cyanobenzyl)-8-(2-hydroxyphenyl)oct-7-enoate

生成物 1

HCID 57831393Ethyl E-8-[2-(4-tert-butylbenzyloxy)phenyl]-6-(4-cyanobenzyl)oct-7-enoate

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A solution of 1.75 g (4.64 mmol) of ethyl E-6-(4-cyanobenzyl)-8-(2-hydroxyphenyl)oct-7-enoate in 50 ml of dry acetonitrile is mixed with 1579 mg (6.95 mmol) of 4-(tert-butyl)benzyl bromide and 961 mg (6.95 mmol) of anhydrous potassium carbonate and heated under reflux for 12 hours. The mixture is then concentrated to dryness. The residue is taken up in ethyl acetate, washed with water and saturated sodium chloride solution and dried over sodium sulfate. The organic phase is concentrated. The resulting crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 8:1→4:1). 2.24 g (4.28 mmol, 92% of theory) of a solid are obtained.

後処理

  1. temperatureheated
  2. temperatureunder reflux for 12 hours
  3. concentrationThe mixture is then concentrated to dryness
  4. washwashed with water and saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. concentrationThe organic phase is concentrated
  7. customThe resulting crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 8:1→4:1)
  8. custom2.24 g (4.28 mmol, 92% of theory) of a solid are obtained

出典と根拠

ORDレコード
ord-4e6d4db233a84338a3185e90ceb811d4
出典データセット
uspto-grants-2012_05
特許番号
US08183271B2

反応ノート

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