Sodium Chloride → HCID 13071115, compound

HRID 1605392Notes

Reaction equation

HRID 1605392 reaction equation
CS(O[CH:6]1[CH2:13][CH:12]2[CH2:14][CH:8]([O:9][CH:10]([CH2:15][O:16][S:17]([CH3:20])(=[O:19])=[O:18])[O:11]2)[CH2:7]1)(=O)=O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(=O)(O)[O-].[Na+].[Cl-].[Na+]>CN(C)C=O.O.CCOCC.C(Cl)Cl>[CH3:20][S:17]([O:16][CH2:15][CH:10]1[O:11][CH:12]2[CH2:14][CH:8]([CH2:7][CH:6]=[CH:13]2)[O:9]1)(=[O:18])=[O:19]

Participants

9

Reactant 4

HCID 5234Sodium ChlorideHCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 13071123HCID 13071123, compound

Product 1

HCID 13071115HCID 13071115, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 660 mg of 7-methylsulphonyloxy-3-methylsulphonyloxymethyl-2,4-dioxabicyclo[3,3,1]nonane of the formula IIb and 1.4 g of tetrabutylammonium fluoride in 7.5 ml of dimethyl formamide is heated under nitrogen for 7 hours to 60°C. The cooled reaction mixture is treated with 20 ml of methylene chloride and 80 ml of ether and shaken successively with 80 ml of an 8% sodium bicarbonate solution, 100 ml of water and 50 ml of sodium chloride solution. The aqueous layers are extracted separately twice with 100 ml of the same solvent mixture on each occasion. The combined organic fractions are dried over sodium sulphate. The solvent is distilled off under reduced pressure to give an oily product whose spectrum properties correspond to those of the pure racemic 3-methylsulphonyloxymethyl-2,4-dioxabicyclo[3,3,1] non-6-ene of the formula IIIa. Preparative chromatography on basic aluminium oxide with benzene as eluant gives the crystalline product of melting point 53°-56° C.

Workup

  1. customThe cooled reaction mixture
  2. extractionThe aqueous layers are extracted separately twice with 100 ml of the same solvent mixture on each occasion
  3. dry with materialThe combined organic fractions are dried over sodium sulphate
  4. distillationThe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-90d2ccfd398e4611b32771d709bbd064
Source dataset
uspto-grants-1976_04
Patent number
US03950362

Reaction notes

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