Tetrahydrofuran → HCID 178487746, compound
Reaction equation
COC1C=[CH:14][C:6]([C:7]([C:9]([N:11](C)C)=N)=O)=[C:5]([CH3:16])C=1.CC(C)([O-:20])C.[K+].[CH2:23]1[CH2:27][O:26][CH2:25][CH2:24]1>>[CH3:25][O:26][C:27]1[CH:14]=[C:6]2[C:7](=[CH:24][CH:23]=1)[C:9]([OH:20])=[N:11][CH:16]=[CH:5]2Participants
4
Conditions
- Temperature
- 30 °C
Procedure
A slurry of 83C (16.33 g) in a small amount of THF (25 mL) was heated to 60° C. in a flask equipped with a stir bar, reflux condenser, and addition funnel. A solution of (1 M potassium tert-butoxide in THF, 105 mL) was titrated in over a period of 30 min. The reaction turned a light yellow, and began to precipitate a solid product after about 10 min and became a thick suspension after 30 min. The reaction was cooled to 30° C. and neutralized to pH 7 with 9.5 mL conc. HCl. Water (about 25 mL) was added to dissolve all the salts, and still an easy phase split remained. The phases were split and the aqueous phase was back extracted with 25 mL ethyl acetate. The organic phases were combined and slowly concentrated at 60° C. to provide a crystalline residue. 12.16 g (93.6%) of 83D was isolated as a light orange solid. An analytical sample was prepared by recrystallization from ethyl acetate. LC retention time=13.533 min. 1H NMR (DMSO-d6) δ 3.86 (s, 3H); 6.46 (d, 1H); 7.02-7.13 (m, 3H), 8.08 (d, 1H); 11.03 (s, 1H).