Ethanol → 4-[4-(1-Isopropoxycyclopropyl)-3-ethyl-phenylethynyl]-benzoic acid

HRID 1935889Notes

Reaction equation

HRID 1935889 reaction equation
[CH:1]([O:4][C:5]1([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[C:15][C:16]3[CH:21]=[CH:20][C:19](CC(OC)=O)=[CH:18][CH:17]=3)=[CH:10][C:9]=2[CH2:27][CH3:28])[CH2:7][CH2:6]1)([CH3:3])[CH3:2].[OH-:29].[Na+].O.CC#N.[CH2:35]([OH:37])C>O1CCCC1>[CH:1]([O:4][C:5]1([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[C:15][C:16]3[CH:17]=[CH:18][C:19]([C:35]([OH:37])=[O:29])=[CH:20][CH:21]=3)=[CH:10][C:9]=2[CH2:27][CH3:28])[CH2:7][CH2:6]1)([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 18373917Acetonitrile--water (1/1)HCID 86585928Methyl{4-[4-(1-isopropoxycyclopropyl)-3-ethyl-phenylethynyl]-phenyl}-acetate2×

Product 1

HCID 225689714-[4-(1-Isopropoxycyclopropyl)-3-ethyl-phenylethynyl]-benzoic acidYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using General Procedure I; a solution of methyl {4-[4-(1-isopropoxycyclopropyl)-3-ethyl-phenylethynyl]-phenyl}-acetate (Compound 96, 156.0 mg, 0.41 mmol) in ethanol (3 mL) and tetrahydrofuran (3 mL) was treated with NaOH (120.0 mg, 3.0 mmols, 3.0 mL of a 1N aqueous solution) and stirred overnight at room temperature. Work-up and isolation by HPLC (partisil 10-pac, 10% H2O/CH3CN) afforded 85.0 mg (57%) of the title compound.

Sources & evidence

ORD record
ord-0e187dccde82452c921451c65098f6ef
Source dataset
uspto-grants-2002_05
Patent number
US06387892B1

Reaction notes

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