Sodium Hydroxide → 4-[4-(1-Benzyloxycyclopropyl)-phenylethynyl]-benzoic acid

HRID 1596945Notes

Reaction equation

HRID 1596945 reaction equation
[CH2:1]([O:8][C:9]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]#[C:19]C3C=CC(CC(OC)=O)=CC=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:31].[Na+]>C(O)C.O1CCCC1>[CH2:1]([O:8][C:9]1([C:12]2[CH:19]=[CH:18][C:15]([C:16]#[C:17][C:5]3[CH:6]=[CH:7][C:2]([C:1]([OH:8])=[O:31])=[CH:3][CH:4]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86585923Methyl{4-[4-(1-benzyloxycyclopropyl)-phenylethynyl]-phenyl}-acetate2×

Product 1

HCID 101336264-[4-(1-Benzyloxycyclopropyl)-phenylethynyl]-benzoic acidYield 81%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Using General Procedure I; a solution of methyl {4-[4-(1-benzyloxycyclopropyl)-phenylethynyl]-phenyl}-acetate (Compound 76, 45.0 mg, 0.11 mmol) in ethanol (3 mL) and tetrahydrofuran (3 mL) was treated with NaOH (80.0 mg, 2.0 mmols, 2.0 mL of a 1N aqueous solution) and stirred overnight at room temperature. Work-up afforded 35.0 mg (81%) of the title compound as a pale-yellow solid.

Sources & evidence

ORD record
ord-04b3975b44e14db4a5bb94ed6075dfcc
Source dataset
uspto-grants-2001_09
Patent number
US06291677B1

Reaction notes

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