Dimethylformamide → HCID 13826318, compound
Reaction equation
[O:1]1CCN=[CH:2]1.[F:6][C:7]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:8]=1[C:9]([OH:11])=[O:10].[Li]C(CC)C.CN(C=O)C>C1COCC1>[F:6][C:7]1[CH:15]=[CH:14][C:13]([F:16])=[C:12]2[C:8]=1[CH:9]([OH:11])[O:10][C:2]2=[O:1]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a -78° C. solution of the oxazoline derivative (7.95 g, 37.7 mmol), prepared from 2,5-difluorobenzoic acid in the usual manner, in THF (50 mL) was added over 15 min sec-BuLi (29 mL of 1.3 M solution). After 30 min, DMF (6.0 mL) was added, and the reaction was stirred at -78° C. for 2 hr. The reaction was tnen quenched with concentrated HCl (5 mL). Tne solvents were removed in vacuo, and the residue was taken up in 5 N HCl (5 mL) and heated on the steam bath overnight. After cooling to room temperature, the reaction mixture was extracted with EtOAc (3×200 mL). Standard workup gave a light brown solid (6.5 g, 93%, mp 125°-128° C.).
Workup
- customThe reaction was tnen quenched with concentrated HCl (5 mL)
- customTne solvents were removed in vacuo
- temperatureheated on the steam bath overnight
- temperatureAfter cooling to room temperature
- extractionthe reaction mixture was extracted with EtOAc (3×200 mL)
Sources & evidence
- ORD record
- ord-bbf9e9b6afc04d8c814b3d2f4c220724
- Source dataset
- uspto-grants-1987_09
- Patent number
- US04697005
Reaction notes
Loading…