Lithium Hydroxide → 3-Cyclopentyl-2-[4-(3-methoxy-prop-1-ynyl)-phenyl]-propionic acid

HRID 1936233Notes

Reaction equation

HRID 1936233 reaction equation
C[O:2][C:3](=[O:22])[CH:4]([C:11]1[CH:16]=[CH:15][C:14]([C:17]#[C:18][CH2:19][O:20][CH3:21])=[CH:13][CH:12]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.[OH-].[Li+]>O1CCCC1.O>[CH:6]1([CH2:5][CH:4]([C:11]2[CH:16]=[CH:15][C:14]([C:17]#[C:18][CH2:19][O:20][CH3:21])=[CH:13][CH:12]=2)[C:3]([OH:22])=[O:2])[CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 674837663-Cyclopentyl-2-[4-(3-methoxy-prop-1-ynyl)-phenyl]-propionic acid methyl ester

Product 1

HCID 224652903-Cyclopentyl-2-[4-(3-methoxy-prop-1-ynyl)-phenyl]-propionic acidYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 3-cyclopentyl-2-[4-(3-methoxy-prop-1-ynyl)-phenyl]-propionic acid methyl ester (485 mg, 1.61 mmol) in tetrahydrofuran (10 mL) and water (10 mL) was treated with lithium hydroxide (775 mg, 18.5 mmol). The reaction mixture was stirred at 25° C. for 48 h. At this time, the reaction was concentrated in vacuo. The residue was re-dissolved in water (40 mL) which was then acidified to pH=2 with concentrated hydrochloric acid. This solution was extracted with ethyl acetate (2×40 mL). The aqueous layers were back extracted with ethyl acetate (1×40 mL). The combined organic extracts were then washed with a half-saturated aqueous sodium chloride solution (1×40 mL), dried over sodium sulfate, filtered, and concentrated in vacuo to afford 3-cyclopentyl-2-[4-(3-methoxy-prop-1-ynyl)-phenyl]-propionic acid (447 mg, 96.7%) as a white solid: mp 82-85° C.; EI-HRMS m/e calcd for C18H22O3 (M+) 286.1568, found 286.1563.

Workup

  1. concentrationAt this time, the reaction was concentrated in vacuo
  2. dissolutionThe residue was re-dissolved in water (40 mL) which
  3. extractionThis solution was extracted with ethyl acetate (2×40 mL)
  4. extractionThe aqueous layers were back extracted with ethyl acetate (1×40 mL)
  5. washThe combined organic extracts were then washed with a half-saturated aqueous sodium chloride solution (1×40 mL)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-63bfed06608e4a2babac3a9a86fc232d
Source dataset
uspto-grants-2002_05
Patent number
US06388071B2

Reaction notes

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