Reaction equation
C(=O)([O-])[O-].[K+].[K+].F[C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1.[CH2:16]([O:18][C:19](=[O:28])[C:20]1[CH:25]=[C:24]([OH:26])[CH:23]=[C:22]([OH:27])[CH:21]=1)[CH3:17]>CN(C=O)C>[CH2:16]([O:18][C:19](=[O:28])[C:20]1[CH:25]=[C:24]([OH:26])[CH:23]=[C:22]([O:27][C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)[CH:21]=1)[CH3:17]Participants
Conditions
- Temperature
- 45 °C
Procedure
Potassium carbonate 6.7 g (48.5 mmol) followed by 4-fluoro benzonitrile 3.3 g (27.2 mmol) in 10 ml of DMF was added to a solution of 3,5-dihydroxy benzoic acid ethyl ester 5 g (27.4 mmol) in 20 ml of DMF at 20° C. The reaction mixture was allowed to attain RT and was then heated to 45° C. for 10 h. The reaction mixture was quenched with ice cold water and extracted with ethyl acetate. The organic layer was washed with water followed by brine, dried over anhydrous sodium sulphate and concentrated. The crude compound was purified by column chromatography using hexane-ethyl acetate (10:2) to afford 1.15 g of the required product. 1H NMR (DMSO-d6): δ 1.3 (3H, t), 4.3 (2H, q), 6.76 (1H, s), 7.02 (1H, s), 7.36 (2H, d), 7.24 (1H, s), 7.88 (2H, d), 10.3 (1H, s).
Workup
- customto attain RT
- customThe reaction mixture was quenched with ice cold water
- extractionextracted with ethyl acetate
- washThe organic layer was washed with water
- dry with materialdried over anhydrous sodium sulphate
- concentrationconcentrated
- customThe crude compound was purified by column chromatography
Sources & evidence
- ORD record
- ord-9aa0e02040034d8faf78beceaba2a0c4
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08722930B2
Linked notes
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