p-Toluenesulfonic acid → HCID 86743428, compound

HRID 1195246Notes

Reaction equation

HRID 1195246 reaction equation
[CH2:1]1[O:3][C@H:2]1[CH2:4][OH:5].[O:6]1[CH:11]=[CH:10][CH2:9][CH2:8][CH2:7]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CCOCC>[CH2:1]1[O:3][CH:2]1[CH2:4][OH:5].[O:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.[CH3:8][CH2:7][O:6][CH2:11][CH3:10]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 6973630(-)-Glycidol

Product 1

HCID 86743428HCID 86743428, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

(S)-Glycidol (2 g, 27.0 mmol) in dihydropyran (40 mL, 438.0 mmol) was treated with para-toluenesulphonic acid (0.3 g, 1.5 mmol) at 0° C. with magnetic stirring. The reaction was complete in 10 minutes (TLC, ether). The reaction mixture was diluted with ether (100 mL), washed with water (10 mL), saturated NaHCO3 solution (20 mL), brine (20 mL) and dried over MgSO4. Concentration and flash chromatography gave the title compound (3 g, 70%).

Workup

  1. washwashed with water (10 mL), saturated NaHCO3 solution (20 mL), brine (20 mL)
  2. dry with materialdried over MgSO4
  3. concentrationConcentration and flash chromatography

Sources & evidence

ORD record
ord-8eeae378cb3749a086ee20d0f0cf8d5d
Source dataset
uspto-grants-1992_05
Patent number
US05110949

Reaction notes

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