Methyl vinyl ketone → Cyclopentanecarboxylic acid, 2-oxo-1-(3-oxobutyl)-, methyl ester

HRID 2202731노트

반응식

HRID 2202731 반응식
[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[C:7]([O:9][CH3:10])=[O:8].[CH:11]([C:13]([CH3:15])=[O:14])=[CH2:12].C(N(CC)CC)C>C1(C)C=CC=CC=1.CCOC(C)=O>[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][C:3]1([CH2:12][CH2:11][C:13](=[O:14])[CH3:15])[C:7]([O:9][CH3:10])=[O:8]

참가 물질

6

반응물 3

HCID 6570Methyl vinyl ketoneHCID 8471TriethylamineHCID 66328Cyclopentanecarboxylic acid, 2-oxo-, methyl ester

생성물 1

HCID 11356301Cyclopentanecarboxylic acid, 2-oxo-1-(3-oxobutyl)-, methyl ester수율 67%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of methyl 2-oxocyclopentanecarboxylate (2.000 ml, 14.07 mmol), methyl vinyl ketone (1.381 ml, 16.88 mmol) and triethylamine (2.94 ml, 21.10 mmol) in toluene (20 mL) was heated at 40° C. for 24 h. The reaction was brought to room temperature, diluted with EtOAc, washed with sat. NH4Cl, dried over Na2SO4, filtered, concentrated and chromatographed on silica gel using 0-50% heptane/EtOAc to afford a colorless oil as methyl 2-oxo-1-(3-oxobutyl)cyclopentanecarboxylate (2.0 g, 9.42 mmol, 67.0% yield).

후처리

  1. customwas brought to room temperature
  2. washwashed with sat. NH4Cl
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customchromatographed on silica gel using 0-50% heptane/EtOAc

출처 및 근거

ORD 기록
ord-a4067a221f594f20a6a5d93cd3ccce91
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09365522B2

반응 노트

불러오는 중…