Water → Ethyl E-6-[2-(4-cyanophenyl)ethyl]-8-(2-hydroxyphenyl)oct-7-enoate

HRID 1927434ノート

反応式

HRID 1927434 の反応式
C([Li])CCC.[Br-].[OH:7][C:8]1[CH:33]=[CH:32][CH:31]=[CH:30][C:9]=1[CH2:10][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[C:34]([C:36]1[CH:41]=[CH:40][C:39]([CH2:42][CH2:43][CH:44]([CH:54]=O)[CH2:45][CH2:46][CH2:47][CH2:48][C:49]([O:51][CH2:52][CH3:53])=[O:50])=[CH:38][CH:37]=1)#[N:35].O>CCCCCC.C1COCC1>[C:34]([C:36]1[CH:41]=[CH:40][C:39]([CH2:42][CH2:43][CH:44](/[CH:54]=[CH:10]/[C:9]2[CH:30]=[CH:31][CH:32]=[CH:33][C:8]=2[OH:7])[CH2:45][CH2:46][CH2:47][CH2:48][C:49]([O:51][CH2:52][CH3:53])=[O:50])=[CH:38][CH:37]=1)#[N:35]

参加物

7

反応物 4

HCID 962WaterHCID 2724142(2-Hydroxybenzyl)triphenylphosphonium bromideHCID 57831367Ethyl 8-(4-cyanophenyl)-6-formyloctanoateHCID 178418339Butyllithium

生成物 1

HCID 57831338Ethyl E-6-[2-(4-cyanophenyl)ethyl]-8-(2-hydroxyphenyl)oct-7-enoate

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

実験手順

5.91 ml (9.45 mmol) of a 1.6 M solution of n-butyllithium in hexane are slowly added to a solution of 1820 mg (4.05 mmol) of (2-hydroxybenzyl)triphenylphosphonium bromide in 15 ml of anhydrous THF at 0° C. Then, at this temperature, a solution of 1085 mg (3.38 mmol) of ethyl 8-(4-cyanophenyl)-6-formyloctanoate in 15 ml of THF is slowly metered in. After the reaction solution has been warmed to room temperature it is stirred for 12 hours and, after addition of some water, concentrated to dryness. The residue is taken up in ethyl acetate, washed with water and saturated sodium chloride solution and dried over sodium sulfate. After filtration, the solvent is concentrated to dryness. The resulting crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 4:1→2:1). 1150 mg (2.79 mmol, 83% of theory) of a colorless solid are obtained.

後処理

  1. concentrationconcentrated to dryness
  2. washwashed with water and saturated sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. filtrationAfter filtration
  5. concentrationthe solvent is concentrated to dryness
  6. customThe resulting crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 4:1→2:1)
  7. custom1150 mg (2.79 mmol, 83% of theory) of a colorless solid are obtained

出典と根拠

ORDレコード
ord-6181287377834dc8964c97d4cb209f95
出典データセット
uspto-grants-2012_05
特許番号
US08183271B2

反応ノート

読み込み中…