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Water → methyl E-4-[3-(4-cyanobenzyl)-5-(2-hydroxyphenyl)pent-4-enyl]benzoate

HRID 1927409
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HRID 1927409 반응식
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:57]=[CH:56][C:39]([CH2:40][CH:41]([CH:54]=O)[CH2:42][CH2:43][C:44]2[CH:53]=[CH:52][C:47]([C:48]([O:50][CH3:51])=[O:49])=[CH:46][CH:45]=2)=[CH:38][CH:37]=1)#[N:35].O>CCCCCC.C1COCC1>[C:34]([C:36]1[CH:37]=[CH:38][C:39]([CH2:40][CH:41](/[CH:54]=[CH:10]/[C:9]2[CH:30]=[CH:31][CH:32]=[CH:33][C:8]=2[OH:7])[CH2:42][CH2:43][C:44]2[CH:45]=[CH:46][C:47]([C:48]([O:50][CH3:51])=[O:49])=[CH:52][CH:53]=2)=[CH:56][CH:57]=1)#[N:35]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 962WaterHCID 2724142(2-Hydroxybenzyl)triphenylphosphonium bromideHCID 57831360Methyl 4-[3-(4-cyanobenzyl)-4-oxobutyl]benzoateHCID 178418339Butyllithium

생성물 1

HCID 57831354methyl E-4-[3-(4-cyanobenzyl)-5-(2-hydroxyphenyl)pent-4-enyl]benzoate

시약·촉매·용매 2

HCID 8028
Tetrahydrofuran
용매
2회
HCID 8058Hexane용매

실험 절차

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 10 ml of anhydrous THF at 0° C. Then, at this temperature, 1085 mg (3.38 mmol) of methyl 4-[3-(4-cyanobenzyl)-4-oxobutyl]benzoate, dissolved in 10 ml of THF, are slowly metered in. After warming to room temperature, the reaction solution is stirred for 12 hours, then some water is added and the mixture is 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.

후처리

  1. concentrationthe mixture is concentrated 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

출처 및 근거

ORD 기록
ord-d0e742ff15e648faad1b30ff919d5e3c
출처 데이터셋
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08183271B2

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