2-Chloro-1,1-dimethoxyethane → 1-(3,3-dimethoxy-1-phenylpropyl)-1H-pyrazole

HRID 1430233

Reaction equation

HRID 1430233 reaction equation
[CH2:1]([N:8]1[CH:12]=[CH:11][CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.Cl[CH2:19][CH:20]([O:23][CH3:24])[O:21][CH3:22]>O1CCCC1>[CH3:22][O:21][CH:20]([O:23][CH3:24])[CH2:19][CH:1]([N:8]1[CH:12]=[CH:11][CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 609862-Chloro-1,1-dimethoxyethaneHCID 35464411-Benzyl-1H-pyrazoleHCID 178418339Butyllithium

Product 1

HCID 866812991-(3,3-dimethoxy-1-phenylpropyl)-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-benzyl-1H-pyrazole (0.653 g) in tetrahydrofuran (5 mL) cooled to −78° C. was dropwise added 1.6M n-butyllithium (2.84 mL). The reaction mixture was stirred for 60 minutes, and 2-chloro-1,1-dimethoxyethane (0.517 mL) was added, and stirring continued for 3 hours. The reaction mixture was allowed to slowly warm up to room temperature, and was quenched with water, extracted with ether, dried over Na2SO4, filtered, and concentrated. The product was purified by chromatography on silica gel using 0-20% ethyl acetate/hexanes as the eluent to provide the title compound.

Workup

  1. stirringstirring
  2. waitcontinued for 3 hours
  3. customwas quenched with water
  4. extractionextracted with ether
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe product was purified by chromatography on silica gel using 0-20% ethyl acetate/hexanes as the eluent

Sources & evidence

ORD record
ord-8cd0504cd5b841509fde464590e420b0
Source dataset
uspto-grants-2015_01
Patent number
US08940737B2

Linked notes

Loading…