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

HRID 381083Notes

Reaction equation

HRID 381083 reaction equation
C([O:3][C:4](=[O:30])[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][CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH2:21][CH2:20]3)=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)C.[OH-].[Na+]>C(O)C.O1CCCC1>[CH2:23]([O:22][C:19]1([C:16]2[CH:17]=[CH:18][C:13]([C:12]#[C:11][C:8]3[CH:7]=[CH:6][C:5]([C:4]([OH:30])=[O:3])=[CH:10][CH:9]=3)=[CH:14][CH:15]=2)[CH2:20][CH2:21]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22568905Ethyl4-[4-(1-benzyloxycyclopropyl)-phenylethynyl]-benzoate2×

Product 1

HCID 101336264-[4-(1-Benzyloxycyclopropyl)-phenylethynyl]-benzoic acidYield 89%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Using General Procedure I; a solution of ethyl4-[4-(1-benzyloxycyclopropyl)-phenylethynyl]-benzoate (Compound 75, 78.0 mg, 0.20 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 65.0 mg (89%) of the title compound as a solid.

Sources & evidence

ORD record
ord-0f1dee6c93eb45b4a270e79f75ef7180
Source dataset
uspto-grants-2001_10
Patent number
US06303785B1

Reaction notes

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