Sodium Hydroxide → HCID 70246342, compound

HRID 381110Notes

Reaction equation

HRID 381110 reaction equation
C([O:3][C:4](=[O:29])[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][CH3:24])[CH2:21][CH2:20]3)=[C:15]([C:25]([CH3:28])([CH3:27])[CH3:26])[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]([CH2:12][CH2:11][C:8]3[CH:7]=[CH:6][C:5]([C:4]([OH:29])=[O:3])=[CH:10][CH:9]=3)=[CH:14][C:15]=2[C:25]([CH3:26])([CH3:28])[CH3:27])[CH2:21][CH2:20]1)[CH3:24]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22568931HCID 22568931, compound2×

Product 1

HCID 70246342HCID 70246342, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Using General Procedure I; a solution of ethyl4-[4-(1-ethoxycyclopropyl)-3-tert-butyl-phenylethynyl]-benzoate (Compound 103, 70.0 mg, 0.18 mmol) in ethanol (3 mL) and tetrahydrofuran (3 mL) was treated with NaOH (240.0 mg, 6.0 mmols, 3.0 mL of a 2N aqueous solution) and stirred overnight at room temperature. Work-up afforded 40 mg (62%) the title compound as a pale-yellow solid.

Sources & evidence

ORD record
ord-d847d28c6c5d4902822a47cc0735ba99
Source dataset
uspto-grants-2001_10
Patent number
US06303785B1

Reaction notes

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