Acetic Acid → 2,2-Dimethyl-5-[4-(trimethylsilanylmethoxy)benzylidene]-1,3-dioxane-4,6-dione

HRID 899018

반응식

HRID 899018 반응식
[CH3:1][Si:2]([CH2:5][O:6][C:7]1[CH:14]=[CH:13][C:10]([CH:11]=O)=[CH:9][CH:8]=1)([CH3:4])[CH3:3].C(=[C:18]([C:22]([O-:24])=[O:23])[C:19]([O-:21])=[O:20])(C)C.N1CC[CH2:28][CH2:27][CH2:26]1.C(O)(=O)C>C1(C)C=CC=CC=1.O>[CH3:26][C:27]1([CH3:28])[O:21][C:19](=[O:20])[C:18](=[CH:11][C:10]2[CH:13]=[CH:14][C:7]([O:6][CH2:5][Si:2]([CH3:4])([CH3:3])[CH3:1])=[CH:8][CH:9]=2)[C:22](=[O:23])[O:24]1

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 23168663IsopropylidenemalonateHCID 565289644-Trimethylsilanylmethoxybenzaldehyde

생성물 1

HCID 103369892,2-Dimethyl-5-[4-(trimethylsilanylmethoxy)benzylidene]-1,3-dioxane-4,6-dione수율 45%

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매

실험 절차

4-(Trimethylsilanylmethoxy)benzaldehyde (obtained in step 1 of Example 1) (5 g, 0.024 mol) and isopropylidenemalonate (3.8 g, 0.0264 mol) in 10 ml of dry toluene in the presence of 0.24 ml of piperidine and 0.14 g of acetic acid are refluxed for 5 hours in a reactor equipped with Dean-Stark apparatus. The water formed is removed azeotropically. The mixture is cooled and the toluene is removed by distillation. The reaction mixture is taken up in 50 ml of diisopropyl ether. The organic phase is washed 3 times with water, dried over sodium sulfate and filtered, and the solvent is evaporated off under vacuum. The yellow oil obtained (7.48 g) is purified by chromatography on a column of silica (eluent: 95/5 heptane/EtOAc). 3.64 g of clean fractions (yield; 45% of the derivative of Example 6 are recovered in the form of a yellow solid:

후처리

  1. customequipped with Dean-Stark apparatus
  2. customis removed azeotropically
  3. temperatureThe mixture is cooled
  4. customthe toluene is removed by distillation
  5. washThe organic phase is washed 3 times with water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customthe solvent is evaporated off under vacuum
  9. customThe yellow oil obtained (7.48 g)
  10. customis purified by chromatography on a column of silica (eluent: 95/5 heptane/EtOAc)
  11. custom3.64 g of clean fractions (yield; 45% of the derivative of Example 6 are recovered in the form of a yellow solid

출처 및 근거

ORD 기록
ord-e3b63b4844aa4913981eeec28ee0fe55
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07354571B2

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