Acetone → Methyl 1-cyanocyclobutane-1-carboxylate
Reaction equation
[C:1]([CH2:3][C:4]([O:6][CH3:7])=[O:5])#[N:2].N12CCCN=C1CC[CH2:11][CH2:10][CH2:9]2.CC(C)=O.BrCCCBr>CN(C=O)C>[CH3:7][O:6][C:4]([C:3]1([C:1]#[N:2])[CH2:11][CH2:10][CH2:9]1)=[O:5]Participants
Conditions
- Temperature
- 50 °C
Procedure
10 g (0.1 mol) of methyl cyanoacetate and 10 mL of anhydrous DMF were mixed under stirring for 10 minutes, followed by adding 33.4 g (0.22 mol) of 1,8-diazabicyclo[5,4,0] undec-7-ene (DBU) at 10-20° C. into the mixture, heating the mixture to 50° C. to allow reaction to take place for 15 minutes, moving the mixture to an ice bath (−5˜−10° C.) of a mixture of liquid nitrogen and acetone, and adding 20.4 g (0.10 mol) of 1,3-dibromopropane dissolved in 10 mL of anhydrous DMF into the mixture to form a reaction solution. The reaction solution was subjected to reaction at 25° C. for 15 minutes, and to further reaction at 70° C. for 30 minutes, followed by evaporating, extracting with CH2Cl2 and deionized water, collecting an organic layer from the extraction, evaporating, purifying using silica column chromatography (eluent: acetone/hexane=8/1), and re-evaporating to obtain a product of 8.74 g (0.063 mol, 62.85%) of 4.
Workup
- customreaction
- customfor 15 minutes
- customto form a reaction solution
- customThe reaction solution was subjected to reaction at 25° C. for 15 minutes
- customto further reaction at 70° C. for 30 minutes
- customby evaporating
- extractionextracting with CH2Cl2
- customcollecting an organic layer
- extractionfrom the extraction
- customevaporating
- custompurifying
- customre-evaporating
Sources & evidence
- ORD record
- ord-55ba8d2473a04ee896027b27cdf05387
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08354512B2
Reaction notes
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