Chloride → 2-(4-Butylphenyl)-1-methoxyethene

HRID 1349367

반응식

HRID 1349367 반응식
[Cl-].C([Li])CCC.[CH2:7]([C:11]1[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=1)[CH2:8][CH2:9][CH3:10].[Cl-].[Na+].[CH2:21]([O:23][CH2:24]C)C>>[CH2:7]([C:11]1[CH:18]=[CH:17][C:14]([CH:15]=[CH:21][O:23][CH3:24])=[CH:13][CH:12]=1)[CH2:8][CH2:9][CH3:10]

참가 물질

6

반응물 5

HCID 312ChlorideHCID 3283Diethyl Ether2회HCID 5234Sodium ChlorideHCID 709884-ButylbenzaldehydeHCID 178418339Butyllithium

생성물 1

HCID 540909372-(4-Butylphenyl)-1-methoxyethene

실험 절차

21.1 g of methoxymethyltriphnylphosphonium chloride is introduced into 280 ml of diethyl ether under nitrogen. At 0° C., 29.6 ml of n-butyllithium solution (1.6 M in hexane) is added in drops, and it is stirred for one hour at room temperature. 10 g of 4-butylbenzaldehyde in 40 ml of diethyl ether is now added, and it is stirred for one more hour. Sodium chloride solution is added to the reaction mixture, extracted with ethyl acetate, dried on sodium sulfate and concentrated by evaporation. After chromatography on silica gel with ethyl acetate, 6.7 g of 2-(4-butylphenyl)-1-methoxyethene 48 (E,Z-mixture) is obtained as a colorless oil, which is dissolved in 200 ml of acetone and is stirred under nitrogen with 10 ml of 2N hydrochloric acid overnight. Sodium chloride solution is added, extracted with ethyl acetate, dried on sodium sulfate and concentrated by evaporation. Chromatographic purification on silica gel with ethyl acetate/hexane yields 3.9 g of title compound 49 as a colorless oil.

후처리

  1. stirringit is stirred for one more hour
  2. extractionextracted with ethyl acetate
  3. customdried on sodium sulfate
  4. concentrationconcentrated by evaporation

출처 및 근거

ORD 기록
ord-57a7b244cb264c7f9a0456e34f2401d2
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07211680B2

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