Water → HCID 86731367, compound

HRID 2277284Notes

Reaction equation

HRID 2277284 reaction equation
Cl[C:2]1[N:7]=[N:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[CH:4][CH:3]=1.[CH:12]1([CH2:15][OH:16])[CH2:14][CH2:13]1.[CH3:17][C:18]([CH3:21])([O-])C.[K+].O>C1COCC1>[CH:12]1([CH2:15][O:16][C:2]2[N:7]=[N:6][C:5]([C:8]([O:10][CH2:11][CH:21]3[CH2:18][CH2:17]3)=[O:9])=[CH:4][CH:3]=2)[CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 962WaterHCID 75644CyclopropanemethanolHCID 12379801Methyl 6-chloropyridazine-3-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 86731367HCID 86731367, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of methyl 6-chloropyridazine-3-carboxylate (1.24 g) and cyclopropylmethanol (1.16 mL) in THF (20 mL) was added potassium tert-butoxide (1.05 g) at −78° C., and the mixture was stirred at the same temperature, allowed to warm to 0° C., and stirred for 3 hr. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (0.48 g).

Workup

  1. stirringstirred for 3 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-dba8ba61a0ee437ab993a6048efc63dd
Source dataset
uspto-grants-2015_09
Patent number
US09133129B2

Reaction notes

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