Methanol → 2-Biphenyl-4-yl-3-cyclopentylpropionic acid methyl ester

HRID 1935266ノート

反応式

HRID 1935266 の反応式
[C:1]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:6]=[CH:5][C:4]([CH:7]([CH2:11][CH:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)[C:8]([OH:10])=[O:9])=[CH:3][CH:2]=1.[CH3:23]O>S(=O)(=O)(O)O>[CH3:23][O:9][C:8](=[O:10])[CH:7]([C:4]1[CH:3]=[CH:2][C:1]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[CH:6][CH:5]=1)[CH2:11][CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16]1

参加物

4

反応物 2

HCID 887MethanolHCID 224679232-Biphenyl-4-yl-3-cyclopentylpropionic acid

生成物 1

HCID 674835462-Biphenyl-4-yl-3-cyclopentylpropionic acid methyl ester収率 95%

試薬・触媒・溶媒 1

HCID 1118Sulfuric Acid触媒

反応条件

温度
25 °C

実験手順

A solution of 2-biphenyl-4-yl-3-cyclopentylpropionic acid (192.3 mg, 0.653 mmol) in methanol (3.3 mL) was treated slowly with concentrated sulfuric acid (1 drop). The resulting reaction mixture was heated under reflux for 24 h. The reaction mixture was allowed to cool to 25° C. and then concentrated in vacuo to remove methanol. The residue was diluted with ethyl acetate (50 mL). The organic phase was washed with a saturated aqueous sodium bicarbonate solution (1×100 mL), water (1×100 mL), and a saturated aqueous sodium chloride solution (1×100 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70-230 mesh, 9/1 hexanes/ethyl acetate) afforded 2-biphenyl-4-yl-3-cyclopentylpropionic acid methyl ester (191.5 mg, 95%) as a yellow oil: EI-HRMS m/e calcd for C21H24O2 (M+) 308.1776, found 308.1774.

後処理

  1. customThe resulting reaction mixture
  2. temperaturewas heated
  3. temperatureunder reflux for 24 h
  4. concentrationconcentrated in vacuo
  5. customto remove methanol
  6. additionThe residue was diluted with ethyl acetate (50 mL)
  7. washThe organic phase was washed with a saturated aqueous sodium bicarbonate solution (1×100 mL), water (1×100 mL)
  8. dry with materialThe organic layer was dried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-88f1268dc089484c836865b7f4704ac9
出典データセット
uspto-grants-2002_05
特許番号
US06384220B2

反応ノート

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