Methanol → Methyl 3-Cyclopropyl-3-(3-hydroxyphenyl)propanoate

HRID 1662371노트

반응식

HRID 1662371 반응식
[CH:1]1([CH:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([OH:15])[CH:10]=2)[CH2:5][C:6]([OH:8])=[O:7])[CH2:3][CH2:2]1.OS(O)(=O)=O.[CH3:21]O>>[CH:1]1([CH:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([OH:15])[CH:10]=2)[CH2:5][C:6]([O:8][CH3:21])=[O:7])[CH2:3][CH2:2]1

참가 물질

4

반응물 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 577059733-Cyclopropyl-3-(3-hydroxyphenyl)propanoic acid

생성물 1

HCID 57706598Methyl 3-Cyclopropyl-3-(3-hydroxyphenyl)propanoate

실험 절차

To a flask containing 3-cyclopropyl-3-(3-hydroxyphenyl)propanoic acid 66.6V (1.2 g, 5.8 mmol) in MeOH (15 mL) was added H2SO4 (0.31 mL, 5.8 mmol). The resulting mixture was stirred at reflux overnight. The reaction was concentrated and purified by combiflash chromatography (0 to 30% EtOAc/Hexanes) to provide methyl 3-cyclopropyl-3-(3-hydroxyphenyl)propanoate 66.6W (1.2 g, 94%). Chiral separation was accomplished on Chiracel-OD (3% IPA in hexane) to provide 66.6X and 66.6Y. Peak 1 was the desired enantiomer. Analytical column (Chiracel-OD (2% IPA in hexane-45 min run) Peak 1-22.5 mins, Peak 2-34.0 mins).

후처리

  1. temperatureat reflux overnight
  2. concentrationThe reaction was concentrated
  3. custompurified by combiflash chromatography (0 to 30% EtOAc/Hexanes)

출처 및 근거

ORD 기록
ord-f0bc6f5db7a84cecaea3420fcb5e68e6
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08030354B2

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