Diethyl methylmalonate → HCID 67466097, compound

HRID 1619933Notes

Reaction equation

HRID 1619933 reaction equation
[K].CC(C)([O-])C.[CH3:7][CH:8]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:9]([O:11][CH2:12][CH3:13])=[O:10].[CH2:19]([N:26]1[C:30]2[CH:31]=[CH:32][C:33]([C:35](=[O:40])[CH:36](Cl)[CH2:37][CH3:38])=[CH:34][C:29]=2[O:28][C:27]1=[O:41])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CS(C)=O.C(O)(=O)C>[CH2:19]([N:26]1[C:30]2[CH:31]=[CH:32][C:33]([C:35]([CH:36]([C:8]([CH3:7])([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:37][CH3:38])=[O:40])=[CH:34][C:29]=2[O:28][C:27]1=[O:41])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 11857Diethyl methylmalonateHCID 50987170Potassium tertbutoxideHCID 86689063HCID 86689063, compound

Product 1

HCID 67466097HCID 67466097, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
40 °C

Procedure

23.00 g (204.96 mmol) potassium-tert.-butoxide are placed in 1200 mL DMSO and 36.00 g (206.67 mmol) diethyl 2-methyl-malonate are added. 64.00 g (194.07 mmol) 3-benzyl-6-(2-chloro-butyryl)-3H-benzoxazol-2-one are added batchwise while being cooled at 40° C. Then the mixture is stirred for 1 h, the reaction mixture is diluted with ice water and neutralised with 15 mL glacial acetic acid. The reaction mixture is extracted with DCM, the org. phase is concentrated by rotary evaporation i. V. and the residue is separated on silica gel (eluant cyclohexane/EA).

Workup

  1. extractionThe reaction mixture is extracted with DCM
  2. concentrationphase is concentrated by rotary evaporation i
  3. customand the residue is separated on silica gel (eluant cyclohexane/EA)

Sources & evidence

ORD record
ord-ad292f3568094bc9a800513ff4f58360
Source dataset
uspto-grants-2014_07
Patent number
US08772323B2

Reaction notes

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