Sodium Hydroxide → 4-[4-(1-Benzyloxycyclopropyl)-3-methyl-phenylethynyl]-benzoic acid

HRID 381086Notes

Reaction equation

HRID 381086 reaction equation
C([O:3][C:4](=[O:31])[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)=[C:15]([CH3:30])[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:31])=[O:3])=[CH:10][CH:9]=3)=[CH:14][C:15]=2[CH3:30])[CH2:21][CH2:20]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22568984Ethyl4-[4-(1-benzyloxycyclopropyl)-3-methyl-phenylethynyl]-benzoate2×

Product 1

HCID 101104414-[4-(1-Benzyloxycyclopropyl)-3-methyl-phenylethynyl]-benzoic acidYield 76%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Using General Procedure I; a solution of ethyl4-[4-(1-benzyloxycyclopropyl)-3-methyl-phenylethynyl]-benzoate (Compound 79, 68.0 mg, 0.17 mmol) in ethanol (3 mL) and tetrahydrofuran (3 mL) was treated with NaOH (360.0 mg, 9.0 mmols, 3.0 mL of a 3N aqueous solution) and stirred overnight at room temperature. Work-up afforded 48.0 mg (76%) of the title compound as a solid.

Sources & evidence

ORD record
ord-6842de1358404b449ebd07582dda15a6
Source dataset
uspto-grants-2001_10
Patent number
US06303785B1

Reaction notes

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