Ethanol → Methyl{4-[4-(1-isopropoxycyclopropyl)-3-ethyl-phenylethynyl]-phenyl}-acetate

HRID 1069941Notes

Reaction equation

HRID 1069941 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:26]=[CH:25][C:19](C(OCC)=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.[CH3:32][C:33]#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:26]=[CH:25][C:19]([CH2:32][C:33]([O:37][CH3:35])=[O:29])=[CH:18][CH:17]=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 22568979Ethyl4-[4-(1-isopropoxycyclopropyl)-3-ethyl-phenylethynyl]-benzoate2×

Product 1

HCID 86585928Methyl{4-[4-(1-isopropoxycyclopropyl)-3-ethyl-phenylethynyl]-phenyl}-acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using General Procedure I; a solution of ethyl 4-[4-(1-isopropoxycyclopropyl)-3-ethyl-phenylethynyl]-benzoate (Compound 95, 110.0 mg, 0.29 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 the title compound as a colorless solid.

Sources & evidence

ORD record
ord-639af8d0343947cb887dad64a2507ae2
Source dataset
uspto-grants-2001_06
Patent number
US06252090B1

Reaction notes

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