Lithium Hydroxide → HCID 22465303, compound

HRID 1936244Notes

Reaction equation

HRID 1936244 reaction equation
C[O:2][C:3](=[O:23])[CH:4]([C:11]1[CH:16]=[CH:15][C:14]([C:17]#[C:18][CH2:19][CH:20]([OH:22])[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][CH:20]([OH:22])[CH3:21])=[CH:13][CH:12]=2)[C:3]([OH:23])=[O:2])[CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67483913HCID 67483913, compound

Product 1

HCID 22465303HCID 22465303, compoundYield 108.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 3-cyclopentyl-2-[4-(4-hydroxy-pent-1-ynyl)-phenyl]-propionic acid methyl ester (545 mg, 1.73 mmol) in tetrahydrofuran (10 mL) and water (10 mL) was treated with lithium hydroxide (830 mg, 19.8 mmol). The reaction mixture was stirred at 25° C. for 3 d. At this time, the reaction was concentrated in vacuo. The residue was diluted with water (40 mL). This solution was acidified to pH=2 with concentrated hydrochloric acid and then extracted with ethyl acetate (2×40 mL). The combined organic extracts were then washed with a half-saturated sodium chloride solution (1×40 mL), dried over sodium sulfate, filtered and concentrated in vacuo to afford 3-cyclopentyl-2-[4-(4-hydroxy-pent-1-ynyl)-phenyl]-propionic acid (565 mg, quant.) as a light brown solid: mp 73-76° C.; EI-HRMS m/e calcd for C19H24O3 (M) 300.1725, found 300.1724.

Workup

  1. concentrationAt this time, the reaction was concentrated in vacuo
  2. additionThe residue was diluted with water (40 mL)
  3. extractionextracted with ethyl acetate (2×40 mL)
  4. washThe combined organic extracts were then washed with a half-saturated sodium chloride solution (1×40 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ebeef0fd13c9401280079188ada73420
Source dataset
uspto-grants-2002_05
Patent number
US06388071B2

Reaction notes

Loading…