Bromide ion → HCID 5088009, compound
Reaction equation
[CH3:1][CH:2]([C:8]([O:10][CH2:11]C)=[O:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].[Br-].O.[CH2:17]1COCC1>>[CH3:17][CH2:1][CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:8]([O:10][CH3:11])=[O:9]Participants
6
Conditions
- Temperature
- 0 °C
Procedure
To a solution of diethyl methylmalonate (5.19 g) in 100 mL of THF was added NaH (1.2 g, 60%) at 0° C. in portions. The mixture was stirred at 0° C. for 10 min, and to this solution was then added the bromide intermediate (3.84 g) in one portion. The mixture was warmed to 23° C. and stirred for 1 h before the addition of water. The resulting mixture was extracted with ethyl acetate, concentrated and purified by Biotage (5-10% ethyl acetate in hexane) to give the diester containing some diethyl methyl malonate contaminant as a crude oil.
Workup
- temperatureThe mixture was warmed to 23° C.
- extractionThe resulting mixture was extracted with ethyl acetate
- concentrationconcentrated
- custompurified by Biotage (5-10% ethyl acetate in hexane)
Sources & evidence
- ORD record
- ord-f2e4dafc28a646ec9c0d8ec300375ff5
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08168649B2
Reaction notes
Loading…