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

HRID 1935269Notes

Reaction equation

HRID 1935269 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Conditions

Temperature
25 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-069aebdd99024531a4b9f85546696474
Source dataset
uspto-grants-2002_05
Patent number
US06384220B2

Reaction notes

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