Hydrochloric Acid → HCID 71272401, compound

HRID 1528069Notes

Reaction equation

HRID 1528069 reaction equation
[C:1]1([N:7]2[CH:11]=[CH:10][CH:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])CCC.CCCCCC.[CH3:23][O:24][CH2:25][CH:26]1[CH2:28][O:27]1.Cl>C1COCC1>[CH3:23][O:24][CH2:25][CH:26]([OH:27])[CH2:28][C:11]1[N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 135891,2-Epoxy-3-methoxypropaneHCID 707691-PhenylpyrazoleHCID 178418244HCID 178418244, compound

Product 1

HCID 71272401HCID 71272401, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To an THF solution (450 ml) of 1-phenylpyrazole (15 g) was added 1.6M butyllithium/hexane solution at −78° C., and the mixture was stirred at −78° C. for 1 hr. To the reaction mixture was added 2-(methoxymethyl)oxirane (27.8 ml) at −78° C., and the mixture was allowed to be warmed to room temperature, and stirred for 1 hr. To the reaction mixture was added 1N hydrochloric acid, the mixture was extracted with ethyl acetate, and the extract was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (12.2 g).

Workup

  1. temperatureto be warmed to room temperature
  2. stirringstirred for 1 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. concentrationthe extract was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-a8cf0e4982974ea59fb9d6cfa3e096a1
Source dataset
uspto-grants-2015_07
Patent number
US09090586B2

Reaction notes

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