Dimethyl Carbonate → Methyl 2-(4-Tert-Butylphenyl)Cyanoacetate

HRID 2183414노트

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HRID 2183414 반응식
[H-].[Na+].[C:3]([C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]#[N:15])=[CH:9][CH:8]=1)([CH3:6])([CH3:5])[CH3:4].[C:16](=O)([O:19]C)[O:17][CH3:18]>O1CCCC1>[C:3]([C:7]1[CH:8]=[CH:9][C:10]([CH:13]([C:14]#[N:15])[C:16]([O:17][CH3:18])=[O:19])=[CH:11][CH:12]=1)([CH3:6])([CH3:4])[CH3:5]

참가 물질

5

반응물 3

HCID 12021Dimethyl CarbonateHCID 24758Sodium hydrideHCID 76784(4-tert-Butylphenyl)acetonitrile

생성물 1

HCID 11701398Methyl 2-(4-Tert-Butylphenyl)Cyanoacetate수율 52%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

0.66 g (16.5 mmols) of sodium hydride and 2.6 g (15.0 mmols) of 4-tert-butylphenylacetonitrile were suspended in 50 ml of tetrahydrofuran. To the suspension was added dropwise 1.95 g (16.5 mmols) of dimethyl carbonate dissolved in 10 ml of tetrahydrofuran while stirring at room temperature. The mixture was refluxed with heating for 2 hours, and the solvent was distilled off under reduced pressure. Water was added to the residue, and the residue was acidified by diluted hydrochloric acid and twice extracted with 30 ml of ethyl acetate. The ethyl acetate extraction solutions were mixed, washed with a saturated brine solution, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue thus-obtained was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1), giving 1.8 g of the desired product (yield 52%)

후처리

  1. temperatureThe mixture was refluxed
  2. temperaturewith heating for 2 hours
  3. distillationthe solvent was distilled off under reduced pressure
  4. additionWater was added to the residue
  5. extractiontwice extracted with 30 ml of ethyl acetate
  6. extractionThe ethyl acetate extraction solutions
  7. additionwere mixed
  8. washwashed with a saturated brine solution
  9. dry with materialdried over anhydrous magnesium sulfate
  10. distillationThe solvent was distilled off under reduced pressure
  11. customThe residue thus-obtained
  12. customwas purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1)

출처 및 근거

ORD 기록
ord-8591238c00b04aaeb7ecd3342e43789f
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06899886B2

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