Ammonium Chloride → Ethyl E-6-(4-cyanobenzyl)-8-(2-hydroxyphenyl)oct-7-enoate

HRID 1672696노트

반응식

HRID 1672696 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:54]=[CH:53][C:39]([CH2:40][CH:41]([CH:51]=O)[CH2:42][CH2:43][CH2:44][CH2:45][C:46]([O:48][CH2:49][CH3:50])=[O:47])=[CH:38][CH:37]=1)#[N:35].[Cl-].[NH4+]>CCCCCC.C1COCC1>[C:34]([C:36]1[CH:54]=[CH:53][C:39]([CH2:40][CH:41](/[CH:51]=[CH:10]/[C:9]2[CH:30]=[CH:31][CH:32]=[CH:33][C:8]=2[OH:7])[CH2:42][CH2:43][CH2:44][CH2:45][C:46]([O:48][CH2:49][CH3:50])=[O:47])=[CH:38][CH:37]=1)#[N:35]

참가 물질

7

반응물 4

HCID 25517Ammonium ChlorideHCID 2724142(2-Hydroxybenzyl)triphenylphosphonium bromideHCID 22560992Ethyl 6-(4-cyanobenzyl)-7-oxoheptanoateHCID 178418339Butyllithium

생성물 1

HCID 57831344Ethyl E-6-(4-cyanobenzyl)-8-(2-hydroxyphenyl)oct-7-enoate수율 32.5%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

실험 절차

15.98 ml (39.95 mmol) of a 2.5 M solution of n-butyllithium in hexane are slowly added to a solution of 6.411 g (14.27 mmol) of (2-hydroxybenzyl)triphenylphosphonium bromide in 300 ml of anhydrous THF at 0° C. Then, at this temperature, 4.1 g (14.27 mmol) of ethyl 6-(4-cyanobenzyl)-7-oxoheptanoate from Example 111A are slowly metered in. After warming to room temperature, the reaction solution is stirred for 12 hours and then mixed with saturated ammonium chloride solution and 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). 1.75 g (4.64 mmol, 32% yield) of a colorless solid are obtained.

후처리

  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)

출처 및 근거

ORD 기록
ord-dccc92ab4f5341aeb74ddfe76d1a23a3
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07998988B2

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