Ethyl 6-(3-tert-butylphenylethynyl)nicotinate → 6-(3-Tert-butylphenylethynyl)nicotinic acid
Reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:11]#[C:12][C:13]2[CH:23]=[CH:22][C:16]([C:17]([O:19]CC)=[O:18])=[CH:15][N:14]=2)[CH:8]=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2]>[OH-].[K+]>[C:1]([C:5]1[CH:6]=[C:7]([C:11]#[C:12][C:13]2[CH:23]=[CH:22][C:16]([C:17]([OH:19])=[O:18])=[CH:15][N:14]=2)[CH:8]=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 60 mg (0.195 mmol) of ethyl 6-(3-tert-butylphenylethynyl)nicotinate (Compound 1) in 4 ml of aqueous ethanolic KOH was stirred at room temperature for 24 hours. The mixture was concentrated in-vacuo and the residue was treated with 5 ml of water and 5 ml of ether. The aqueous layer was separated and washed with a further 5 ml of ether. The aqueous layer was then acidified with 3 ml of 10 percent HCl and extracted with 2×5 ml of ether. The ether extracts were combined and washed with saturated NaCl solution and then dried (MgSO4). The solution was concentrated in-vacuo to give the title compound as a pale yellow solid. PMR (CDCl3): & 1.26 (9H, s), 7.25 (1H, t, J~7.8 Hz), 7.35-7.42 (2H, m), 7.56-7.63 (2H, m), 8.35 (1H, dd, J~8.2H, 2.1 Hz), 9.31 (1H, d, J~2.1 Hz).
Workup
- concentrationThe mixture was concentrated in-vacuo
- additionthe residue was treated with 5 ml of water and 5 ml of ether
- customThe aqueous layer was separated
- washwashed with a further 5 ml of ether
- extractionextracted with 2×5 ml of ether
- washwashed with saturated NaCl solution
- dry with materialdried (MgSO4)
- concentrationThe solution was concentrated in-vacuo
Sources & evidence
- ORD record
- ord-d682cb944a0a47358d003c99970b0917
- Source dataset
- uspto-grants-1995_05
- Patent number
- US05414007
Reaction notes
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