Lithium Hydroxide → HCID 22467935, compound

HRID 1935197Notes

Reaction equation

HRID 1935197 reaction equation
C[O:2][C:3](=[O:27])[CH:4]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=[CH:19][CH:18]=2)=[CH:13][CH:12]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.[OH-].[Li+]>O1CCCC1>[CH:6]1([CH2:5][CH:4]([C:11]2[CH:12]=[CH:13][C:14]([C:17]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH:20]=[CH:19][CH:18]=3)=[CH:15][CH:16]=2)[C:3]([OH:27])=[O:2])[CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67483520HCID 67483520, compound

Product 1

HCID 22467935HCID 22467935, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 3-cyclopentyl-2-(4-naphthalen-1-yl-phenyl)-propionic acid methyl ester (3.32 g, 9.26 mmol) in tetrahydrofuran (12 mL) was treated with a 0.8M aqueous lithium hydroxide solution (12 mL). The resulting reaction mixture was stirred at 25° C. for 24 h, at which time, thin layer chromatography indicated the presence of starting material. The reaction mixture was then heated at 80° C. for 18 h. The reaction mixture was then allowed to cool to 25° C. and concentrated in vacuo to remove tetrahydrofuran. The residue was acidified to pH=2 with a 10% aqueous hydrochloric acid solution and then extracted with ethyl acetate (2×150 mL). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70-230 mesh, 3/1 hexanes/ethyl acetate) afforded 3-cyclopentyl-2-(4-naphthalen-1-yl-phenyl)-propionic acid (1.74 g, 55%) as a white foam: mp 63-64° C.; EI-HRMS m/e calcd for C24H24O2 (M+) 344.1776, found 344.1770.

Workup

  1. customThe resulting reaction mixture
  2. temperatureThe reaction mixture was then heated at 80° C. for 18 h
  3. temperatureto cool to 25° C.
  4. concentrationconcentrated in vacuo
  5. customto remove tetrahydrofuran
  6. extractionextracted with ethyl acetate (2×150 mL)
  7. dry with materialThe combined organic extracts were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1a4fafb39ec34855bc20d72f3ea99cd4
Source dataset
uspto-grants-2002_05
Patent number
US06384220B2

Reaction notes

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