Tetrahydrofuran → HCID 12927583, compound
Reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][CH:9]=[O:10])=[C:6]([Cl:11])[N:5]=[CH:4][N:3]=1.[CH2:12]1COCC1.[N+](=C)=[N-]>C(OCC)C>[Cl:11][C:6]1[C:7]([CH2:8][C:9](=[O:10])[CH3:12])=[C:2]([Cl:1])[N:3]=[CH:4][N:5]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A 500 mL two necked round bottom flask was charged with 2-(4,6-dichloropyrimidin-5-yl)acetaldehyde (1.2 g), dry diethyl ether (80 mL) and dry THF (80 mL). The reaction mixture was cooled to 0° C. and diazomethane solution in diethyl ether (30 mL) was slowly added under nitrogen atmosphere at 0° C. The reaction mixture was stirred at room temperature for 24 hours under nitrogen atmosphere before being quenched by acetic acid (20 mL), followed by water (100 mL). Aqueous layer was extracted with dichloromethane (2×25 mL). The combined organic layer was washed with brine (50 mL) and dried over anhydrous Na2SO4. Evaporation of solvents under reduced pressure gave crude 1-(4,6-dichloropyrimidin-5-yl)propan-2-one (0.94 g) which was used as was. 1H NMR (DMSO-d6): δ 2.32 (s, 3H), 4.19 (s, 2H), 8.85 (s, 1H).
Workup
- custombefore being quenched by acetic acid (20 mL)
- extractionAqueous layer was extracted with dichloromethane (2×25 mL)
- washThe combined organic layer was washed with brine (50 mL)
- dry with materialdried over anhydrous Na2SO4
- customEvaporation of solvents under reduced pressure
Sources & evidence
- ORD record
- ord-936318a9b3ae443aac6be25fe71211ab
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09193725B2
Reaction notes
Loading…