Water → {5-[1-(t-Butyldimethylsilanyloxy)ethyl]isoxazol-3-yl}methyl 4-methylbenzenesulfonate

HRID 2261347Notes

Reaction equation

HRID 2261347 reaction equation
[Si:1]([O:8][CH:9]([C:11]1[O:15][N:14]=[C:13]([CH2:16][OH:17])[CH:12]=1)[CH3:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].N12CCN(CC1)CC2.[C:26]1([CH3:36])[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1.O>COC(C)(C)C>[CH3:36][C:26]1[CH:31]=[CH:30][C:29]([S:32]([O:17][CH2:16][C:13]2[CH:12]=[C:11]([CH:9]([O:8][Si:1]([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3])[CH3:10])[O:15][N:14]=2)(=[O:34])=[O:33])=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 9237DabcoHCID 57736294{5-[1-(t-Butyldimethylsilanyloxy)ethyl]isoxazol-3-yl}methanol

Product 1

HCID 57736329{5-[1-(t-Butyldimethylsilanyloxy)ethyl]isoxazol-3-yl}methyl 4-methylbenzenesulfonateYield 30.6%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

7.35 g of {5-[1-(t-butyldimethylsilanyloxy)ethyl]isoxazol-3-yl}methanol was dissolved in 50 ml of methyl-t-butyl ether, and 3.36 g of 1,4-diazabicyclo[2.2.2]octane and 5.72 g of 4-toluenesulfonyl chloride were then added under ice-cooling. The mixture was stirred for 10 hours under ice-cooling. After water was added, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 3.60 g of {5-[1-(t-butyldimethylsilanyloxy)ethyl]isoxazol-3-yl}methyl 4-methylbenzenesulfonate.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1405339cffb74d65b89d3e585416405a
Source dataset
uspto-grants-2010_12
Patent number
US07846956B2

Reaction notes

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