Hydrochloric Acid → (R)-3-methoxydihydro-2H-pyran-4(3H)-one

HRID 1400071Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1400071
C[C:2]([CH3:5])([O-:4])C.[Na+].S([O:12][CH3:13])(OC)(=O)=O.Cl.C([O-])(O)=O.[Na+].[O:20]1[CH2:24]C[CH2:22][CH2:21]1>O>[CH3:24][O:20][C@H:21]1[C:13](=[O:12])[CH2:5][CH2:2][O:4][CH2:22]1

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 6497Dimethyl SulfateHCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 23676156Sodium t-butoxide

Produkt 1

HCID 11320949(R)-3-methoxydihydro-2H-pyran-4(3H)-oneAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of the product from step 3 (9.5 g, 64.68 mol) in tetrahydrofuran (300 mL) was added sodium tert-butoxide (9.3 g, 97.02 mmol) at ice bath. Then dimethyl sulfate (13.4 g, 106 mmol) was added over 20 minutes, maintaining an internal temp below 36° C. After addition, the reaction mixture was stirred for 4 hours at room temperature. Water (200 mL) was added followed by addition of 2N HCl (100 mL). The apparent pH was below 1. After 16 hours of reaction, NaHCO3 (20 g) was added and the mixture was extracted with ethyl acetate (4×300 mL), dried over Na2SO4, filtered, and concentrated to an oil (6 g, yield: 71%).

Aufarbeitung

  1. temperaturemaintaining an internal temp below 36° C
  2. additionAfter addition
  3. additionwas added
  4. extractionthe mixture was extracted with ethyl acetate (4×300 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-239558108bf84f098b147c3fb956b91b
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08906911B2

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