Water → (1-(Cyanomethyl)cyclopropyl)methyl acetate
Reaction equation
[C-]#N.[K+].[CH3:4][N:5](C=O)C.[C:9]([O:12][CH2:13][C:14]1([CH2:17]Br)[CH2:16][CH2:15]1)(=[O:11])[CH3:10].O>C1(C)C=CC=CC=1>[C:9]([O:12][CH2:13][C:14]1([CH2:17][C:4]#[N:5])[CH2:16][CH2:15]1)(=[O:11])[CH3:10]Participants
Conditions
- Temperature
- 80 °C
Procedure
A 12 L 4-neck round bottle flask was equipped with mechanical stirrer, a thermometer, a condenser, a nitrogen inlet and an additional funnel. To the flask was charged 1335 mL of and 667 g of potassium cyanide and kept stirring to complete dissolution. 1417 g of DMF and 1417 g of crude [1-(bromomethyl)cyclopropyl]methyl acetate were added from the addition funnel over 30 min. When the addition was complete, the reaction mixture was heated to 80° C. with stirring about 1 hour. The resulting mixture was cooled to about 20˜25° C. 3500 mL of water and 3500 mL of toluene were added to the reaction mixture with stirring over 30 min. The layers were separated and the aqueous layer was back extracted with 3500 mL of toluene. Combined the organic layer and then concentrated to obtain 1253 g dark brown liquid.
Workup
- customA 12 L 4-neck round bottle flask was equipped with mechanical stirrer
- additionWhen the addition
- stirringwith stirring about 1 hour
- temperatureThe resulting mixture was cooled to about 20˜25° C
- stirringwith stirring over 30 min
- customThe layers were separated
- extractionthe aqueous layer was back extracted with 3500 mL of toluene
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-4d6e3f7a32f6458cb231b4ddcca3588b
- Source dataset
- uspto-grants-2007_09
- Patent number
- US07271268B1
Reaction notes
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