Dimethyl Sulfate → HCID 69124508, compound

HRID 656250Notes

Reaction equation

HRID 656250 reaction equation
[OH-].[Na+].S(OC)(O[CH3:7])(=O)=O.[OH:10][C@H:11]1[CH2:16][O:15][CH2:14][C@@H:13]([C:17]([O:19][CH3:20])=[O:18])[CH2:12]1>[Br-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C1(C)C=CC=CC=1.O.C(OCC)(=O)C>[CH3:7][O:10][C@H:11]1[CH2:16][O:15][CH2:14][C@@H:13]([C:17]([O:19][CH3:20])=[O:18])[CH2:12]1

Participants

8

Reactant 3

HCID 6497Dimethyl Sulfate2×HCID 14798Sodium HydroxideHCID 691244671,5-Anhydro-2,3-dideoxy-2-(methoxycarbonyl)-erythropentitol

Product 1

HCID 69124508HCID 69124508, compound

Reagents, catalysts & solvents 4

HCID 165294Benzyltriethylammonium bromideCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

15 ml of 50% NaOH, 367 mg of benzyltriethylammonium bromide and 0.95 ml of dimethyl sulphate are added to a solution of 1.05 g of methyl (cis)-5-hydroxytetrahydropyran-3-carboxylate in 30 ml of toluene. The two-phase mixture is stirred at room temperature for 18 hours. A further 1 ml of dimethyl sulphate is added. The mixture is stirred at room temperature for a further 6 hours, then diluted with water and ethyl acetate, and stirred at room temperature for 20 minutes. The phases are separated, and the aqueous phase is extracted with ethyl acetate. The combined organic phases are washed with brine, dried with sodium sulphate and evaporated. The crude title compound is identified. by means of the Rf from the residue.

Workup

  1. stirringThe mixture is stirred at room temperature for a further 6 hours
  2. stirringstirred at room temperature for 20 minutes
  3. customThe phases are separated
  4. extractionthe aqueous phase is extracted with ethyl acetate
  5. washThe combined organic phases are washed with brine
  6. dry with materialdried with sodium sulphate
  7. customevaporated

Sources & evidence

ORD record
ord-591d744b13d045e6a8ca546186057807
Source dataset
uspto-grants-2011_12
Patent number
US08071651B2

Reaction notes

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