Sodium Hydroxide → {4-[4-(1-Methoxycyclopropyl)phenylethynyl]-phenyl}-acetic acid

HRID 24142Notes

Reaction equation

HRID 24142 reaction equation
C[O:2][C:3](=[O:24])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3([O:22][CH3:23])[CH2:21][CH2:20]3)=[CH:15][CH:14]=2)=[CH:7][CH:6]=1.[OH-].[Na+]>C(O)C.O1CCCC1>[CH3:23][O:22][C:19]1([C:16]2[CH:15]=[CH:14][C:13]([C:12]#[C:11][C:8]3[CH:7]=[CH:6][C:5]([CH2:4][C:3]([OH:24])=[O:2])=[CH:10][CH:9]=3)=[CH:18][CH:17]=2)[CH2:21][CH2:20]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86585921Methyl{4-[4-(1-methoxycyclopropyl)-phenylethynyl]-phenyl}-acetate2×

Product 1

HCID 9879577{4-[4-(1-Methoxycyclopropyl)phenylethynyl]-phenyl}-acetic acidYield 84.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Using General Procedure I; a solution of methyl{4-[4-(1-methoxycyclopropyl)-phenylethynyl]-phenyl}-acetate (Compound 68, 100.0 mg, 0.31 mmol) in ethanol (3 mL) and tetrahydrofuran (3 mL) was treated with NaOH (160.0 mg, 4.0 mmols, 2.0 mL of a 2N aqueous solution) and stirred overnight at room temperature. Work-up afforded 80.0 mg (84%) of the title compound as an orange solid.

Sources & evidence

ORD record
ord-4a6e9ce34f2e4fbb819b13c844778755
Source dataset
uspto-grants-2005_02
Patent number
US06855512B2

Reaction notes

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