Dimethyl Sulfoxide → HCID 13483105, compound

HRID 2305823Notes

Reaction equation

HRID 2305823 reaction equation
C[C:2](C)([O-:4])C.[K+].[N+:7]([CH2:10][CH2:11][CH3:12])([O-])=O.[C:13]([C:15](=[C:20]([CH3:22])[CH3:21])[C:16](OC)=O)#N.CS(C)=[O:25]>>[C:10]([C:11]1([C:12]([O:4][CH3:2])=[O:25])[C:20]([CH3:22])([CH3:21])[C:15]1([CH3:16])[CH3:13])#[N:7]

Participants

5

Reactant 4

HCID 679Dimethyl Sulfoxide3×HCID 79031-NitropropaneHCID 248907methyl 2-cyano-3-methylbut-2-enoateHCID 23665647Potassium tert-butoxide

Product 1

HCID 13483105HCID 13483105, compound

Procedure

The title compound was synthesized similarly to J. Org. Chem. 50 (1985), 2807-2809: 5.6 g (50mmol) of potassium tert-butoxide were initially charged in 15 ml of dimethyl sulfoxide, and 4.4 g (50 mmol) of nitropropane dissolved in 190 ml of dimethyl sulfoxide were slowly added dropwise. After addition of 5 g (36 mmol) of methyl 2-cyano-3-methylbut-2-enoate dissolved in 10 ml of dimethyl sulfoxide, the mixture was stirred at room temperature for 40 hours. The reaction was quenched by slow addition of water. The reaction mixture was extracted three times with methyl tert-butyl ether. The organic phases were dried with magnesium sulfate and freed from ether giving the crude product (9 g), which was employed for the next reaction without any further purification.

Workup

  1. additionwere slowly added dropwise
  2. customThe reaction was quenched by slow addition of water
  3. extractionThe reaction mixture was extracted three times with methyl tert-butyl ether
  4. dry with materialThe organic phases were dried with magnesium sulfate
  5. customwas employed for the next reaction without any further purification

Sources & evidence

ORD record
ord-d596ae9026f747309866659b016b572f
Source dataset
uspto-grants-2002_08
Patent number
US06441044B1

Reaction notes

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