Nitrogen → 2-(2-Methyl[1,3]dioxolane-2-yl)furan

HRID 42745

Reaction equation

HRID 42745 reaction equation
N#N.[O:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[C:8](=[O:10])[CH3:9].COC([O:16][CH3:17])OC.[C:18]([O-])(O)=O.[Na+]>C(O)CO>[O:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[C:8]1([CH3:9])[O:16][CH2:17][CH2:18][O:10]1

Participants

6

Reactant 4

HCID 947NitrogenHCID 9005Trimethyl orthoformateHCID 145052-AcetylfuranHCID 516892Sodium Bicarbonate

Product 1

HCID 117448352-(2-Methyl[1,3]dioxolane-2-yl)furan

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
95 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 1-furan-2-yl-ethanone (50.00 g, 454.0 mmol) in ethylene glycol (500.0 mL) was treated with trimethylorthoformate (100.0 mL, 908.0 mmol) followed by LiBF4 (7.00 g, 75 mmol). The reaction mixture was heated at 95° C. overnight. Sat. aq. NaHCO3 (500 mL) was added and the mixture was extracted with EA (500 mL). The org. extracts were washed with brine (2×250 mL), dried over MgSO4, filtered, and the solvent was removed under reduced pressure. Purification of the residue by distillation (11 mbar, 71-73° C.) gave the title compound as a colorless oil.

Workup

  1. extractionthe mixture was extracted with EA (500 mL)
  2. washextracts were washed with brine (2×250 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure
  6. customPurification of the residue
  7. distillationby distillation (11 mbar, 71-73° C.)

Sources & evidence

ORD record
ord-2c8f0b2cbdf5456fa3f70c2d09e31f41
Source dataset
uspto-grants-2013_09
Patent number
US08536209B2

Linked notes

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