Butyric Acid → methyl 4-acetyltetrahydro-2H-pyran-4-carboxylate

HRID 2088876Notes

Reaction equation

HRID 2088876 reaction equation
[C:1]([OH:6])(=O)[CH2:2][CH2:3][CH3:4].Cl[CH2:8][CH2:9][O:10][CH2:11][CH2:12]Cl.C(=O)([O-])[O-:15].[K+].[K+].[I-].[Na+].CN(C)[CH:24]=[O:25]>>[C:3]([C:2]1([C:1]([O:25][CH3:24])=[O:6])[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1)(=[O:15])[CH3:4]

Participants

6

Reactant 5

HCID 264Butyric AcidHCID 5238Sodium Iodide2×HCID 6228DimethylformamideHCID 8115Bis(2-chloroethyl) etherHCID 11430Potassium Carbonate2×

Product 1

HCID 9964279methyl 4-acetyltetrahydro-2H-pyran-4-carboxylate

Conditions

Temperature
80 °C

Procedure

Add butanoic acid, 3-oxo-, methyl ester (18.60 mL, 172.20 mmol), bis(2-chloroethyl)ether (20.20 mL, 1.0 eq), potassium carbonate (52.42 g, 2.2 eq), and sodium iodide (25.88 g, 1.0 eq) in dimethylformamide (861 mL). Heat the reaction mixture at 80° C. overnight. Cool to room temperature. Add additional potassium carbonate (23.78 g) and sodium iodide (25.88 g). Heat the reaction mixture at 80° C. for two hours, then allow the mixture to cool to room temperature. Filter through Celite® and wash with ethyl acetate. Wash the filtrate with water and brine. Dry the organics over anhydrous sodium sulfate, filter, and concentrate in vacuo to give methyl 4-acetyltetrahydro-2H-pyran-4-carboxylate (23.06 g).

Workup

  1. temperatureCool to room temperature
  2. temperatureHeat the reaction mixture at 80° C. for two hours
  3. temperatureto cool to room temperature
  4. filtrationFilter through Celite®
  5. washwash with ethyl acetate
  6. washWash the filtrate with water and brine
  7. dry with materialDry the organics over anhydrous sodium sulfate
  8. filtrationfilter
  9. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-923146994d2c46efb99dd89341ca3148
Source dataset
uspto-grants-2013_05
Patent number
US08436002B2

Reaction notes

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