Dimethyl Sulfate → HCID 12148220, compound

HRID 574869Notes

Reaction equation

HRID 574869 reaction equation
[CH:1]([C:3]1([OH:9])[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1)=[CH2:2].[H-].[Na+].S(OC)(O[CH3:16])(=O)=O.[NH4+].[Cl-]>O1CCCC1>[CH3:16][O:9][C:3]1([CH:1]=[CH2:2])[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 3135164-ethenyloxan-4-ol

Product 1

HCID 12148220HCID 12148220, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of EXAMPLE 234A (9.4 g) in tetrahydrofuran (150 mL) was added 60% sodium hydride (5.28 g) at 0° C. portionwise. After the addition was complete, the solution was heated under reflux for three hours. After cooling, to this suspension was added dimethyl sulfate (8.41 mL) slowly. The solution was heated under reflux overnight, cooled to room temperature, and hydrolyzed with cool saturated aqueous NH4Cl. After extraction with diethyl ether several times, the combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified by flash column chromatograph on silica gel using 1-10% ethyl acetate in hexanes to provide the title compound.

Workup

  1. additionAfter the addition
  2. temperaturethe solution was heated
  3. temperatureunder reflux for three hours
  4. temperatureAfter cooling, to this suspension
  5. temperatureThe solution was heated
  6. temperatureunder reflux overnight
  7. extractionAfter extraction with diethyl ether several times
  8. washthe combined organic layers were washed with brine
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe residue was purified by flash column chromatograph on silica gel using 1-10% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-9af07a0a218f4ae793b802dc6d34a3db
Source dataset
uspto-grants-2015_05
Patent number
US09034875B2

Reaction notes

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