Methanesulfonyl chloride → HCID 247764, compound

HRID 2231625Notes

Reaction equation

HRID 2231625 reaction equation
[CH3:1][C:2]1([CH3:11])[O:6][C@H:5]([CH2:7][OH:8])[C@@H:4]([CH2:9][OH:10])[O:3]1.[CH3:12][S:13](Cl)(=[O:15])=[O:14].C(=O)(O)[O-].[Na+]>N1C=CC=CC=1>[CH3:1][C:2]1([CH3:11])[O:3][C@H:4]([CH2:9][O:10][S:13]([CH3:12])(=[O:15])=[O:14])[C@@H:5]([CH2:7][O:8][S:13]([CH3:12])(=[O:15])=[O:14])[O:6]1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 78524473346-74-4

Product 1

HCID 247764HCID 247764, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The starting material (1) (3,4-O-isopropylidene-D-mannitol) was reacted with sodium periodate and potassium borohydride as described in J. Chem. Soc., Perkin Trans. I., 1972, 275 (the contents of which are herein incorporated by reference) to yield compound (2) in 92% yield. Compound (2) (5.1 g) was dissolved in pyridine (40 ml) and cooled in ice. To this solution was added methanesulphonyl chloride (18 ml), dropwise with stirring. The mixture was allowed to stand at room temperature for 3 hours, after which time it was added to a solution of sodium bicarbonate. This solution was then extracted with dichloromethane (5×50 ml) and the combined extracts were dried (MgSO4) and concentrated in vacuo. The residue obtained was recrystallised from ethanol to give 2,3-O-isopropylidene-1,4-di-O-methanesulphonyl-D-threitol (3), (6.6 g, 66%), m.p. 83°-85° C.

Workup

  1. temperaturecooled in ice
  2. extractionThis solution was then extracted with dichloromethane (5×50 ml)
  3. dry with materialthe combined extracts were dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue obtained
  6. customwas recrystallised from ethanol

Sources & evidence

ORD record
ord-00b19121bf104c5b9bddcf2665e67340
Source dataset
uspto-grants-1988_11
Patent number
US04783452

Reaction notes

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