Hydrochloric Acid → 2-[4-(2-Methylbutyryl)benzyl]anisole

HRID 895649노트

반응식

HRID 895649 반응식
C(N(CC)[C:4]([C:6]1[CH:20]=[CH:19][C:9]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:17][CH3:18])=[CH:8][CH:7]=1)=[O:5])C.[CH:23]([Li])([CH2:25][CH3:26])[CH3:24].Cl>C1(C)C=CC=CC=1.CCCCCC.C1CCCCC1>[CH3:24][CH:23]([CH2:25][CH3:26])[C:4]([C:6]1[CH:7]=[CH:8][C:9]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:17][CH3:18])=[CH:19][CH:20]=1)=[O:5]

참가 물질

7

반응물 3

HCID 313Hydrochloric AcidHCID 223806822-(4-Diethylcarbamoylbenzyl)anisoleHCID 178418400CID 53628100

생성물 1

HCID 223805962-[4-(2-Methylbutyryl)benzyl]anisole수율 61%

시약·촉매·용매 3

HCID 1140Toluene용매HCID 8058Hexane용매HCID 8078Cyclohexane용매

실험 절차

The 2-(4-diethylcarbamoylbenzyl)anisole (100 mg) obtained in the process of Reference Example 1(d) was dissolved in toluene (2 ml), added with a solution of sec-butyl lithium in n-hexane and cyclohexane (1.0 M, 0.47 ml) at 0° C. under argon atmosphere and stirred at room temperature for 1 hour. After the reaction mixture was slowly poured into 1 N aqueous hydrochloric acid (5 ml) with ice cooling to quench the reaction and the layers were separated, the aqueous layer was extracted with ether (10 ml). The organic layer was washed with saline and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by preparative thin layer silica gel column chromatography (developing solvent: hexane:ethyl acetate=2:1) to obtain 58.3 mg of the title compound. Yield: 61%.

후처리

  1. customto quench
  2. customthe reaction
  3. customthe layers were separated
  4. extractionthe aqueous layer was extracted with ether (10 ml)
  5. washThe organic layer was washed with saline
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by preparative thin layer silica gel column chromatography (developing solvent: hexane:ethyl acetate=2:1)

출처 및 근거

ORD 기록
ord-74a497591a954d9d989c51a3d92f9b12
출처 데이터셋
uspto-grants-2005_07
특허 번호
US06916822B2

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