Water → 5-(3-(((Tert-butyldiphenylsilyl)oxy)methyl)benzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione

HRID 1049405

반응식

HRID 1049405 반응식
[CH3:1][C:2]1([CH3:10])[O:9][C:7](=[O:8])[CH2:6][C:4](=[O:5])[O:3]1.[Si:11]([O:28][CH2:29][C:30]1[CH:31]=[C:32]([CH:35]=[CH:36][CH:37]=1)[CH:33]=O)([C:24]([CH3:27])([CH3:26])[CH3:25])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.N1C=CC=CC=1.O>C1COCC1.[Ti](Cl)(Cl)(Cl)Cl>[Si:11]([O:28][CH2:29][C:30]1[CH:31]=[C:32]([CH:35]=[CH:36][CH:37]=1)[CH:33]=[C:6]1[C:7](=[O:8])[O:9][C:2]([CH3:10])([CH3:1])[O:3][C:4]1=[O:5])([C:24]([CH3:27])([CH3:25])[CH3:26])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

참가 물질

7

반응물 4

HCID 962Water2회HCID 1049PyridineHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 10883279Benzaldehyde, 3-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-

생성물 1

HCID 1317360095-(3-(((Tert-butyldiphenylsilyl)oxy)methyl)benzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione수율 73.7%

시약·촉매·용매 2

HCID 24193Titanium Tetrachloride촉매HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

To a solution of titanium (IV) chloride (9.88 g) in THF (80 mL) were added dropwise a solution of meldrum's acid (3.75 g) and 3-(((tert-butyldiphenylsilyl)oxy)methyl)benzaldehyde (6.50 g) in THF (50 mL) at 0° C., and pyridine (11.0 g) was further added dropwise at 0° C. over 30 min. The reaction mixture was stirred at 0° C. for 50 min, and water (100 mL) was added dropwise at 0° C. over 5 min. Water was further added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (6.40 g) as a white amorphous solid.

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-325c835c56d845f49cbb99b683699d24
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09382188B2

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