4-Toluenesulfonyl chloride → HCID 53798011, compound

HRID 1510466Notes

Reaction equation

HRID 1510466 reaction equation
[O:1]1[CH2:5][C@@H:4]([OH:6])[C@H:3]2[O:7][CH2:8][C@H:9]([OH:10])[C@@H:2]12.[S:11](Cl)([C:14]1[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=1)(=[O:13])=[O:12].[OH-].[K+]>O.C1(C)C=CC=CC=1>[CH3:18][C:17]1[CH:19]=[CH:20][C:14]([S:11]([O:6][C@H:4]2[CH2:5][O:1][C@@H:2]3[C@H:9]([OH:10])[CH2:8][O:7][C@H:3]23)(=[O:13])=[O:12])=[CH:15][CH:16]=1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 12597IsosorbideHCID 14797Potassium Hydroxide

Product 1

HCID 53798011HCID 53798011, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

In a 2 L flask, 100.0 g (0.684 mol) of (3R,3aR,6S,6aR)-hexahydrofuro[3,2-b]furan-3,6-diol (Isosorbide) were dissolved in 600 ml of water and 130, 5 g (0.684 mol) of Tosyl chloride dissolved in 600 ml of Toluene are added at 0° C. 49.5 g (0.751 mol) of potassium hydroxide (86%) in 170 ml of water were added dropwise over ½ h at 0° C. and the reaction was stirred for 1 hr at 0° C. and 5 h at room temperature. The organic phase was extracted, dried, filtered and concentrated under vacuum and after subjecting the crude reaction product to silica gel column chromatography and eluting with a 99/1 mixture of dichloromethane/methyl alcohol, 50.0 g of the product of the title were obtained after concentrating to dryness.

Workup

  1. additionare added at 0° C
  2. extractionThe organic phase was extracted
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customreaction product to silica gel column chromatography
  7. washeluting with a 99/1 mixture of dichloromethane/methyl alcohol, 50.0 g of the product of the title
  8. customwere obtained
  9. concentrationafter concentrating to dryness

Sources & evidence

ORD record
ord-31e20794650e4c378613f40ee678e79a
Source dataset
uspto-grants-2012_07
Patent number
US08211939B2

Reaction notes

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