Sodium hydride → 1-[2-(4-tert-Butoxyphenoxy)ethoxy]-1H-pyrazole

HRID 1588299Notes

Reaction equation

[OH:1][N:2]1[CH:6]=[CH:5][CH:4]=[N:3]1.[H-].[Na+].[CH3:9][C:10]([CH3:23])([O:12][C:13]1[CH:22]=[CH:21][C:16]([O:17][CH2:18][CH2:19]Br)=[CH:15][CH:14]=1)[CH3:11]>CN(C=O)C>[CH3:23][C:10]([CH3:9])([O:12][C:13]1[CH:22]=[CH:21][C:16]([O:17][CH2:18][CH2:19][O:1][N:2]2[CH:6]=[CH:5][CH:4]=[N:3]2)=[CH:15][CH:14]=1)[CH3:11]

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of 12.7 g (0.15 mol) of N-hydroxypyrazole in 20 ml of DMF was added dropwise to a suspension of 4.95 g (1.1 eq.) of NaH (80% dispersion in mineral oil) in 40 ml of DMF at RT, and the mixture was heated at 70° C. for 1 h. A solution of 40.95 g (0.15 mol) of 2-[4-(1,1-dimethylethoxy)phenoxy]ethyl bromide in 100 ml of DMF was added and the mixture was then heated at 125° C. for 15 h. The solvent was then stripped off in a rotary evaporator, the residue was taken up in ethyl acetate, and the solution was washed twice each with 5% strength NaOH solution and water. Drying and removal of the solvent under reduced pressured resulted in 38.4 g (93%) of the required compound as a pale oil which was employed without further purification in the next stage.

Workup

temperaturethe mixture was then heated at 125° C. for 15 h
customThe solvent was then stripped off in a rotary evaporator
washthe solution was washed twice each with 5% strength NaOH solution and water
customDrying
customremoval of the solvent

Sources & evidence

ORD record: ord-eebd2dd53b924a1fb391c924852a6e9f
Source dataset: uspto-grants-1993_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05221684

Reaction notes

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