4,5-Dihydro-2,4,4-trimethyloxazole → 2-(4-tert-Butyldiphenylsilyloxy-2-hydroxybutyl)-4,4-dimethyl-2-oxazoline

HRID 1417479

반응식

HRID 1417479 반응식
C([Li])CCC.[CH3:6][C:7]1[O:8][CH2:9][C:10]([CH3:13])([CH3:12])[N:11]=1.[Si:14]([O:31][CH2:32][CH2:33][CH:34]=[O:35])([C:27]([CH3:30])([CH3:29])[CH3:28])([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CCCCCC.O1CCCC1.O>[Si:14]([O:31][CH2:32][CH2:33][CH:34]([OH:35])[CH2:6][C:7]1[O:8][CH2:9][C:10]([CH3:13])([CH3:12])[N:11]=1)([C:27]([CH3:29])([CH3:30])[CH3:28])([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

참가 물질

7

반응물 3

HCID 744964,5-Dihydro-2,4,4-trimethyloxazoleHCID 9995679Propanal, 3-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-HCID 178418339Butyllithium

생성물 1

HCID 542337122-(4-tert-Butyldiphenylsilyloxy-2-hydroxybutyl)-4,4-dimethyl-2-oxazoline수율 80%

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

반응 조건

온도
-78 °C

실험 절차

5.2 ml of a solution of 1.6M n-butyllithium in hexane was added dropwise to a solution of 940 mg of 2,4,4-trimethyl-2-oxazoline in 20 ml of tetrahydrofuran with stirring, at -78° C. The resulting mixture was stirred at -78° C. for 1 hour. After this time, 2.00 g of 3-tert-butyldiphenylsilyloxy-1-propanal [prepared as described in Can. J. Chem., 71, 695 (1993)] in 10 ml of tetrahydrofuran was added to the reaction mixture whilst stirring, maintaining the temperature at -78° C. Stirring was continued at -78° C. for 15 minutes, then the reaction mixture was brought to room temperature and stirred for 30 minutes. At the end of this time, the reaction mixture was diluted with water and extracted with ethyl acetate. The ethyl acetate fraction was washed with water, dried over anhydrous sodium sulfate and the solvent removed by evaporation under reduced pressure. The resulting residue was purified by silica gel column chromatography, using a mixture of 50% v/v ethyl acetate and hexane as the eluent, to afford 2.18 g of the title compound as an oil.

후처리

  1. stirringThe resulting mixture was stirred at -78° C. for 1 hour
  2. stirringwhilst stirring
  3. temperaturemaintaining the temperature at -78° C
  4. stirringStirring
  5. customwas brought to room temperature
  6. stirringstirred for 30 minutes
  7. extractionextracted with ethyl acetate
  8. washThe ethyl acetate fraction was washed with water
  9. dry with materialdried over anhydrous sodium sulfate
  10. customthe solvent removed by evaporation under reduced pressure
  11. customThe resulting residue was purified by silica gel column chromatography
  12. additiona mixture of 50% v/v ethyl acetate and hexane as the eluent

출처 및 근거

ORD 기록
ord-69aca421515840b78c88582a9c670b76
출처 데이터셋
uspto-grants-1999_03
특허 번호
US05877199

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