4-Toluenesulfonyl chloride → HCID 86736662, compound

HRID 426725Notes

Reaction equation

HRID 426725 reaction equation
[OH:1][C:2]1[O:9][C@H:8]([CH2:10][OH:11])[CH2:7][C@H:5]([OH:6])[C:3]=1[OH:4].[S:12](Cl)([C:15]1[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=1)(=[O:14])=[O:13]>N1C=CC=CC=1>[S:12]([O:11][CH2:10][C@H:8]1[O:9][C:2]([OH:1])=[C:3]([OH:4])[C@@H:5]([OH:6])[CH2:7]1)([C:15]1[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=1)(=[O:14])=[O:13]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 70605833HCID 70605833, compound

Product 1

HCID 86736662HCID 86736662, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Dissolve 10 gm. of the alcohol and 15.4 gm. of tosyl chloride in 100 ml. of dry pyridine and let the solution stand at 25°C. for 17 hours. Add ethanol and evaporate the solution to a residue and then azeotrope with toluene. Chromatograph the residue on a silica gel column (110 × 2.5 cm) using 10% acetone in hexane as the eluant to obtain 4-deoxy-6O-tosyl-D-threo-hex-1-enopyranose.

Workup

  1. dissolutionDissolve 10 gm
  2. customat 25°C.
  3. customfor 17 hours
  4. customAdd ethanol and evaporate the solution to a residue

Sources & evidence

ORD record
ord-06ecafa9c09e40a496e0b2307915ec26
Source dataset
uspto-grants-1979_10
Patent number
US04171356

Reaction notes

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