Ethyl Acetate → 3-[3-(4,5-Diphenyloxazol-2-yl)-3-hydroxy-2-(2-hydroxyethyl)propyl]-1-(t-butyldiphenylsilyloxy)benzene

HRID 1741355Notes

Reaction equation

HRID 1741355 reaction equation
[C:1]1([C:7]2[N:8]=[CH:9][O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])CCC.[Si:23]([O:40][C:41]1[CH:42]=[C:43]([CH:51]=[CH:52][CH:53]=1)[CH2:44][CH:45]1[CH2:49][CH2:48][O:47][C:46]1=[O:50])([C:36]([CH3:39])([CH3:38])[CH3:37])([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(OCC)(=O)C>C1COCC1.O>[C:1]1([C:7]2[N:8]=[C:9]([CH:46]([OH:50])[CH:45]([CH2:49][CH2:48][OH:47])[CH2:44][C:43]3[CH:42]=[C:41]([O:40][Si:23]([C:36]([CH3:38])([CH3:39])[CH3:37])([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[CH:53]=[CH:52][CH:51]=3)[O:10][C:11]=2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 6134984,5-DiphenyloxazoleHCID 183672193-(3-t-Butyldiphenylsilyloxybenzyl)-2-oxotetrahydrofuranHCID 178418339Butyllithium

Product 1

HCID 183674053-[3-(4,5-Diphenyloxazol-2-yl)-3-hydroxy-2-(2-hydroxyethyl)propyl]-1-(t-butyldiphenylsilyloxy)benzeneYield 85.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4,5-diphenyloxazole (5.3 g) in THF (50 ml) at -78° C. under N2 was added n-butyllithium (1.6 M in hexane, 9.2 ml). After 30 minutes, a solution of 3-(3-t-butyldiphenylsilyloxybenzyl)-2-oxotetrahydrofuran (3.3 g) in THF (30 ml) was added thereto and stirred for 1 hour at the same temperature. The reaction mixture was poured into the mixture of ethyl acetate and water. The organic layer was washed with 1N-HCl solution, sat. NaHCO3 and brine, dried over MgSO4, and evaporated in vacuo. The oily residue was dissolved in THF (100 ml) and LiAlH4 was added to the solution at 0° C. After being stirred for 2 hours, the mixture was poured into a mixture of ethyl acetate and 1N-HCl solution. The organic layer was washed with sat. NaHCO3 and brine, dried over MgSO4, and evaporated in vacuo. The residue was purified by chromatography on silica gel to afford 3-[3-(4,5-diphenyloxazol-2-yl)-3-hydroxy-2-(2-hydroxyethyl)propyl]-1-(t-butyldiphenylsilyloxy)benzene (4.3 g). MS (m/z): 654 (M+ +1) IR (Neat): 3400 cm-1NMR (CDCl3, δ): 1.09 (9H, s), 1.4-1.8 (2H, m), 2.2-2.7 (3H, m), 3.3-3.8 (2H, m), 4.6-4.8 (1H, m), 6.5-6.8 (3H, m), 6.99 (1H, t, J=8 Hz), 7.2-7.8 (20H, m)

Workup

  1. washThe organic layer was washed with 1N-HCl solution, sat. NaHCO3 and brine
  2. dry with materialdried over MgSO4
  3. customevaporated in vacuo
  4. dissolutionThe oily residue was dissolved in THF (100 ml)
  5. additionLiAlH4 was added to the solution at 0° C
  6. stirringAfter being stirred for 2 hours
  7. additionthe mixture was poured into a mixture of ethyl acetate and 1N-HCl solution
  8. washThe organic layer was washed with sat. NaHCO3 and brine
  9. dry with materialdried over MgSO4
  10. customevaporated in vacuo
  11. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-263c492134b14e78a6a9ea9639d6bebb
Source dataset
uspto-grants-1999_10
Patent number
US05972965

Reaction notes

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