HCID 59457726, compound → HCID 59457678, compound
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]#[C:9][Si](C)(C)C)[C:3]=1[CH2:14][C:15]([O:17]CC)=[O:16]>[OH-].[Na+].CO>[C:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[C:3]=1[CH2:14][C:15]([OH:17])=[O:16])#[CH:9]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A stirred solution of 331 (607 mg, 2.18 mmol) and IN NaOH (5.5 mL) in methanol (15 mL) was heated at 45° C. for 16 h under nitrogen. The reaction mixture was allowed to cool to room temperature; it was then concentrated, diluted with water, and washed with hexanes. The aqueous layer was collected, acidified with 3N HCl and extracted twice with AcOEt. The organic extract was dried over anhydrous magnesium sulfate, filtered, and concentrated to afford title compound 332 (400 mg, 94% yield, mono-hydrate) as an orange sticky solid. LCMS: 201.1 (M+Na)+.