Methanesulfonyl chloride → HCID 13071123, compound

HRID 267259Notes

Reaction equation

HRID 267259 reaction equation
[OH:1][CH2:2][CH:3]1[O:10][CH:9]2[CH2:11][CH:5]([CH2:6][CH:7]([OH:12])[CH2:8]2)[O:4]1.[CH3:13][S:14](Cl)(=[O:16])=[O:15]>N1C=CC=CC=1>[CH3:13][S:14]([O:12][CH:7]1[CH2:8][CH:9]2[CH2:11][CH:5]([O:4][CH:3]([CH2:2][O:1][S:14]([CH3:13])(=[O:16])=[O:15])[O:10]2)[CH2:6]1)(=[O:16])=[O:15]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 13071121HCID 13071121, compound

Product 1

HCID 13071123HCID 13071123, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 0.87 g (5 mmols) of 3-hydroxymethyl-2,4-dioxabicyclo[3,3,1]nonan-7-ol of the formula IIa in 5 ml of anhydrous pyridine is cooled to -20°C and, while stirring, treated with 1,1 ml (14,2 mmols) of methanesulphonyl chloride. The cooling bath is removed and the reaction mixture is added after 11/4 hours to 40 ml of a normal sodium bicarbonate solution. The resulting mixture is extracted successively with 40 ml of ethyl acetate and 40 ml of methylene chloride. The combined organic solutions are washed with 10 ml of sodium bicarbonate solution, dried over magnesium sulphate and concentrated in a water jet vacuum. The crude product is recrystallised from acetone/heptane and gives 7-methylsulphonyloxy-3-methylsulphonyloxymethyl-2,4-dioxabicyclo[3,3,1]nonane of the formula IIb ##SPC10##

Workup

  1. customThe cooling bath is removed
  2. additionthe reaction mixture is added after 11/4 hours to 40 ml of a normal sodium bicarbonate solution
  3. extractionThe resulting mixture is extracted successively with 40 ml of ethyl acetate and 40 ml of methylene chloride
  4. washThe combined organic solutions are washed with 10 ml of sodium bicarbonate solution
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated in a water jet vacuum
  7. customThe crude product is recrystallised from acetone/heptane

Sources & evidence

ORD record
ord-4a8a54ca9c3f47318ebb2e7190447813
Source dataset
uspto-grants-1976_03
Patent number
US03941813

Reaction notes

Loading…