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

HRID 1662371ノート

反応式

HRID 1662371 の反応式
[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

参加物

4

反応物 3

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

生成物 1

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

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-f0bc6f5db7a84cecaea3420fcb5e68e6
出典データセット
uspto-grants-2011_10
特許番号
US08030354B2

反応ノート

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