Methanol → 2,5-Dihydro-2,5-dimethoxyfuran

HRID 1377829

Reaction equation

HRID 1377829 reaction equation
[C:1](=[O:4])([O-:3])[O-].[Na+].[Na+].C[C:8]1[O:12][C:11](CCCOC2C(C)=CC(C3N=NN(C)N=3)=CC=2C)=[CH:10][CH:9]=1.BrBr.[CH3:33]O>[Cl-].[Na+].O>[CH3:33][O:3][CH:1]1[CH:9]=[CH:10][CH:11]([O:12][CH3:8])[O:4]1

Participants

6

Reactant 4

HCID 887Methanol2×HCID 10340Sodium CarbonateHCID 24408BromineHCID 52730885-[3,5-Dimethyl-4-[3-(5-methyl-2-furyl)propoxy]phenyl]-2-methyl-tetrazole

Product 1

HCID 789742,5-Dihydro-2,5-dimethoxyfuran

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

Sodium carbonate (1.2 g) was added to a cooled (-10° C.) solution of 5-methyl 2-[3-[2,6-dimethyl-4-(2-methyl-tetrazol-5-yl)phenoxy]-propyl]furan from example 9d (780 mg, 2.4 mmol) in 18 mL of methanol with stirring, and then bromine (0.135 g, 14 mmol) in 8 mL of methanol was added dropwise until the brown color persisted, and the resulting reaction mixture was allowed to stir at -10° C. for 45 min. To the mixture was added brine, extracted with ether (3×25 mL), and the organic layer was washed with water, dried over magnesium sulfate, and concentrated in vacuo to yield an oil which was purified by MPLC chromatography (ethyl acetate/hexane 3:7) to afford 820 mg (76.3%) of 5-methyl-2-[3-[2,6-dimethyl-4-]2-methyl-tetrazol-5-yl)phenoxy]-propyl]-2,5-dimethoxy-2,5-dihydrofuran.

Workup

  1. customthe resulting reaction mixture
  2. stirringto stir at -10° C. for 45 min
  3. extractionextracted with ether (3×25 mL)
  4. washthe organic layer was washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customto yield an oil which
  8. customwas purified by MPLC chromatography (ethyl acetate/hexane 3:7)

Sources & evidence

ORD record
ord-3b95d288b8c447cca9dc9b813654b2ff
Source dataset
uspto-grants-1997_09
Patent number
US05665763

Linked notes

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