Water → Ethyl 4-cyanooxane-4-carboxylate
Reaction equation
[C:1]([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].N12CCCN=C1CCCCC2.[O:20]([CH2:24][CH2:25]Br)[CH2:21][CH2:22]Br.O>CN(C=O)C>[C:1]([C:3]1([C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:25][CH2:24][O:20][CH2:21][CH2:22]1)#[N:2]Participants
6
Conditions
- Temperature
- 0 °C
Procedure
A solution of ethyl cyanoacetate (7.0 g) and 1,8-diazabicyclo[5,4,0]undec-7-ene (19 mL) in DMF (310 mL) was stirred at room temperature for 10 min, and cooled to 0° C. To this mixture was added 1,1′-oxybis(2-bromoethane) (15.8 g) at 0° C., and the mixture was stirred at 80° C. for 4 hr and cooled to room temperature. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, dried and concentrated under reduced pressure to give ethyl 4-cyanotetrahydro-2H-pyran-4-carboxylate (10.1 g, 89%) as a deep brown oil.
Workup
- temperaturecooled to room temperature
- extractionthe mixture was extracted with ethyl acetate
- washThe extract was washed with water and saturated brine
- customdried
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-da2033dc30064471bb879f44cf0302a4
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08592454B2
Reaction notes
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