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

HRID 899018ノート

反応式

HRID 899018 の反応式
[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

参加物

7

反応物 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 23168663IsopropylidenemalonateHCID 565289644-Trimethylsilanylmethoxybenzaldehyde

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

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:

後処理

  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

出典と根拠

ORDレコード
ord-e3b63b4844aa4913981eeec28ee0fe55
出典データセット
uspto-grants-2008_04
特許番号
US07354571B2

反応ノート

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