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

HRID 1672675ノート

反応式

HRID 1672675 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収率 64.7%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

実験手順

15.91 ml (25.45 mmol) of a 1.6 M solution of n-butyllithium in hexane are slowly added to a solution of 5.066 g (10.91 mmol) of (2-hydroxybenzyl)triphenylphosphonium bromide in 38 ml of anhydrous THF at 0° C. Then, at this temperature, 2.740 g (9.09 mmol) of ethyl 8-(4-cyanophenyl)-6-formyloctanoate from Example 86A, dissolved in 38 ml of THF, are 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 10:1→4:1). 2.30 g (5.88 mmol, 63% yield) 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 10:1→4:1)

出典と根拠

ORDレコード
ord-a5018439b4154f40b0a5691879db1584
出典データセット
uspto-grants-2011_08
特許番号
US07998988B2

反応ノート

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