Dimethyl Sulfate → HCID 69420203, compound

HRID 1268711Notes

Reaction equation

HRID 1268711 reaction equation
[CH3:1][C:2]1([CH3:12])[O:6][C@H:5]2[CH2:7][S:8][C@H:9]([CH:10]=[O:11])[C@H]2O1.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.S([O:39][CH3:40])(OC)(=O)=O.[C:41](=O)([O-])[O-:42].[K+].[K+]>CN(C)C=O.CC(C)=O.O>[CH3:41][O:42][C:10]([C@@H:9]1[C@@H:40]2[C@@H:5]([O:6][C:2]([CH3:1])([CH3:12])[O:39]2)[CH2:7][S:8]1)=[O:11]

Participants

8

Reactant 4

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 2724130Cornforth reagentHCID 86601630HCID 86601630, compound

Product 1

HCID 69420203HCID 69420203, compoundYield 132%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2.8 g (0.015 mol) of (3aS,4S,6aR)-2,2-dimethyltetrahydrothieno[3,4-d][1,3]dioxole-4–Carbaldehyde from the aforementioned Experimental Example 6 were dissolved in 200 mL of anhydrous N,N-dimethylformamide to which 26.7 g (0.070 mol) of pyridinium dichromate was added. The reaction mixture was stirred at ambient temperature for 20 h. After 0.3 L of water were added, it was extracted with 2.5 L of ethyl acetate (0.5 L×5). The extract was dried, filtered, and concentrated under reduced pressure to obtain the concentrate which was (3aS,4S,6aR)-2,2-dimethyltetrahydrothieno[3,4-d][1,3]dioxole-4-carboxylic acid. The concentrate was dissolved in 65 mL of acetone to which 2 mL (21.14 mmol) of dimethyl sulfate and 1.2 g (8.68 mmol) of potassium carbonate were added. The resulting mixture was stirred for 2 h. Acetone was distilled off under reduced pressure, and the residue was dissolved in ethyl acetate, followed by washing with water and saturated saline solution. The organic layer was dried and filtered, and the filtrate was concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography using the eluant (hexane:ethyl acetate=3:1) mixture to obtain 2.5 g (yield: 78%) of (3aS,4S,6aR)-2,2-dimethyltetrahydrothieno[3,4-d][1,3]dioxole-4-carboxylic acid methyl ester as an oil.

Workup

  1. additionwas added
  2. extractionit was extracted with 2.5 L of ethyl acetate (0.5 L×5)
  3. customThe extract was dried
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto obtain the
  7. concentrationconcentrate which
  8. additionwere added
  9. stirringThe resulting mixture was stirred for 2 h
  10. distillationAcetone was distilled off under reduced pressure
  11. dissolutionthe residue was dissolved in ethyl acetate
  12. washby washing with water and saturated saline solution
  13. customThe organic layer was dried
  14. filtrationfiltered
  15. concentrationthe filtrate was concentrated under reduced pressure
  16. customThe concentrate was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-44e7db3daed241f28e9969950ab613e9
Source dataset
uspto-grants-2007_04
Patent number
US07199127B2

Reaction notes

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