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

HRID 1417479Notes

Reaction equation

HRID 1417479 reaction equation
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

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-69aca421515840b78c88582a9c670b76
Source dataset
uspto-grants-1999_03
Patent number
US05877199

Reaction notes

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