6-Oxabicyclo[3.1.0]hexane → HCID 89962390, compound

HRID 337717Notes

Reaction equation

HRID 337717 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[N:3]1.C([Li])CCC.[CH:12]12[O:17][CH:13]1[CH2:14][CH2:15][CH2:16]2.C(=O)([O-])O.[Na+]>C1COCC1>[CH3:1][N:2]1[C:6]([C@H:12]2[CH2:16][CH2:15][CH2:14][C@@H:13]2[OH:17])=[CH:5][CH:4]=[N:3]1

Participants

6

Reactant 4

HCID 92446-Oxabicyclo[3.1.0]hexaneHCID 702551H-Pyrazole, 1-methyl-HCID 516892Sodium BicarbonateHCID 178418339Butyllithium

Product 1

HCID 89962390HCID 89962390, compoundYield 21.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-methylpyrazole (13.4 g, 163 mmol) in THF (1 L), n-butyl lithium (1.63 M solution in hexane; 100 mL, 163 mmol) was added dropwise at −78° C. for 40 minutes. To the reaction solution, cyclopentene oxide (15.1 g, 179 mmol) was added at −78° C., and the reaction solution was stirred at room temperature for 20 hours. To the reaction solution, a saturated aqueous solution of sodium hydrogencarbonate (100 mL) was added, followed by extraction with ethyl acetate (500 mL). The thus obtained organic layer was dried over anhydrous sodium sulfate. After vacuum concentration, the residue was purified with silica gel chromatography (dichloromethane/methanol=97:3) to yield the title compound (5.77 g, 21%) as a colorless oil.

Workup

  1. extractionfollowed by extraction with ethyl acetate (500 mL)
  2. dry with materialThe thus obtained organic layer was dried over anhydrous sodium sulfate
  3. concentrationAfter vacuum concentration
  4. customthe residue was purified with silica gel chromatography (dichloromethane/methanol=97:3)

Sources & evidence

ORD record
ord-20a4a3f837224531b38cea0a439af46a
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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