Tetrahydrofuran → HCID 66868250, compound
Reaction equation
[CH3:1][C:2]([CH3:5])([O-])[CH3:3].[K+].CC(P(OC)(O)=O)([C:10]([O-:12])=[O:11])C.CC(C1[CH:26]=[CH:25][C:24]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)=[CH:23][CH:22]=1)=O.[CH2:33]1COCC1>Cl>[CH3:33][O:12][C:10](=[O:11])[CH:1]=[C:2]([C:5]1[CH:26]=[CH:25][C:24]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)=[CH:23][CH:22]=1)[CH3:3]Participants
Procedure
To a chilled (0° C.) solution of potassium tert-butoxide (1.0 M, 37.1 mL) was dropwise added a solution of trimethylphosphonoacetate, keeping the temperature below 25° C. The solution was then allowed to warm to room temperature and stirred for an additional five minutes, after which a solution of 4-morpholinoacetophenone in THF (20 mL) was added in one portion. The solution was slowly heated to 60° C. for 36 hours. The solution was cooled to room temperature, then diluted with a 1.0N HCl solution (100 mL), and extracted with ethyl acetate (2×100 mL). The organic layers were combined and dried over MgSO4, filtered, and the filtrate concentrated to a white solid which was recrystallized from hexane/ethyl acetate to give 3.33 grams of 3-(4-morpholinophenyl)but-2-enoic acid methyl ester intermediate (69.9% yield).
Workup
- customthe temperature below 25° C
- temperatureThe solution was slowly heated to 60° C. for 36 hours
- temperatureThe solution was cooled to room temperature
- extractionextracted with ethyl acetate (2×100 mL)
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationthe filtrate concentrated to a white solid which
- customwas recrystallized from hexane/ethyl acetate
Sources & evidence
- ORD record
- ord-29173d97f6c147938cf46dae0fbbfe42
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09212155B2
Reaction notes
Loading…