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

HRID 278707Notes

Reaction equation

HRID 278707 reaction equation
[CH3:1][O:2][C:3]1([C:6]2[CH:11]=[CH:10][C:9]([C:12]#[C:13][C:14]3[CH:19]=[CH:18][C:17]([CH2:20][C:21]([O:23]C)=[O:22])=[CH:16][CH:15]=3)=[CH:8][CH:7]=2)[CH2:5][CH2:4]1.[OH-].[Na+]>C(O)C.O1CCCC1>[CH3:1][O:2][C:3]1([C:6]2[CH:7]=[CH:8][C:9]([C:12]#[C:13][C:14]3[CH:15]=[CH:16][C:17]([CH2:20][C:21]([OH:23])=[O:22])=[CH:18][CH:19]=3)=[CH:10][CH:11]=2)[CH2:5][CH2:4]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-5e8d102cd25a45e7b1a84b0f4c117cee
Source dataset
uspto-grants-2002_03
Patent number
US06359135B1

Reaction notes

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