Dimethylformamide → Methyl 3-cyano-4-hydroxybenzoate
Reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1I.[H-].[Na+].[CH3:15][N:16](C=O)C>>[C:15]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:2]=1[OH:1])[C:6]([O:8][CH3:9])=[O:7])#[N:16]Participants
4
Procedure
A solution of compound 2 (6.46 g, 24.1 mmol) in DMF (30 mL) was treated with sodium hydride (1.94 g of 60% dispersion in mineral oil, 48.6 mmol) portionwise at room temperature. The resulting mixture was stirred at room temperature for 16 hours and then partitioned between water (100 mL) and EtOAc (350 mL). The layers were separated, and the organic layer was washed with water (4×150 mL). The organic phase was dried (Na2SO4) and concentrated to a white solid. Compound 3 (5.56 g, 24.0 mmol, quantitative yield) was dried under high vacuum and characterized using 1H NMR. It was used in the following step without further purification.
Workup
- custompartitioned between water (100 mL) and EtOAc (350 mL)
- customThe layers were separated
- washthe organic layer was washed with water (4×150 mL)
- dry with materialThe organic phase was dried (Na2SO4)
- concentrationconcentrated to a white solid
Sources & evidence
- ORD record
- ord-975fcee181db4d02ab6f576cb6b6217e
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07582668B2
Reaction notes
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