Water → 2-Phenyl-3-t-butyl-5-p-toluenesulfonyloxymethyloxazolidine

HRID 26720Notes

Reaction equation

HRID 26720 reaction equation
[C:1]1([CH:7]2[N:11]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:10][CH:9]([CH2:16][OH:17])[O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:18]1([CH3:28])[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1.O>C(N(CC)CC)C>[C:1]1([CH:7]2[N:11]([C:12]([CH3:13])([CH3:14])[CH3:15])[CH2:10][CH:9]([CH2:16][O:17][S:24]([C:21]3[CH:22]=[CH:23][C:18]([CH3:28])=[CH:19][CH:20]=3)(=[O:26])=[O:25])[O:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 1088103-(1,1-Dimethylethyl)-2-phenyloxazolidine-5-methanol

Product 1

HCID 125837332-Phenyl-3-t-butyl-5-p-toluenesulfonyloxymethyloxazolidine

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a solution of dl-2-phenyl-3-t-butyl-5-hydroxymethyloxazolidine (12.05 g.) in triethylamine (120 ml.) 13 is added p-toluenesulfonylchloride (14.5 g.). After 6 days at room temperature the mixture is added to water (500 ml.) and extracted with ether (2×200 ml.). The ether solution is washed with water, dried with anhydrous magnesium sulfate and evaporated to dryness. The residue is recrystallized from hexane to afford 2-phenyl-3-t-butyl-5-p-toluenesulfonyloxymethyloxazolidine.

Workup

  1. extractionextracted with ether (2×200 ml.)
  2. washThe ether solution is washed with water
  3. dry with materialdried with anhydrous magnesium sulfate
  4. customevaporated to dryness
  5. customThe residue is recrystallized from hexane

Sources & evidence

ORD record
ord-8d9cadbdf09c4fe3a8cb4f6f4140267a
Source dataset
uspto-grants-1979_04
Patent number
US04151297

Reaction notes

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