Sodium hydride → 1-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-yl)ethanone

HRID 2093662Notes

Reaction equation

[H-].[Na+].Cl.[NH:4]1[C:8]([C:9](=[O:11])[CH3:10])=[CH:7][CH:6]=[N:5]1.[CH3:12][Si:13]([CH3:20])([CH3:19])[CH2:14][CH2:15][O:16][CH2:17]Cl>C1COCC1>[CH3:12][Si:13]([CH3:20])([CH3:19])[CH2:14][CH2:15][O:16][CH2:17][N:4]1[C:8]([C:9](=[O:11])[CH3:10])=[CH:7][CH:6]=[N:5]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of sodium hydride (3.07 g, 76.75 mmol) in 100 mL of anhydrous THF cooled to 0° C. under N2 (g) inlet was added 1-(1H-pyrazole-5-yl)ethan-1-one hydrochloride (3.09 g, 21.08 mmol). After warming to rt over 1 h, a solution of 2-(trimethylsilyl)ethoxymethyl chloride (4.5 mL, 25.43 mmol) in 100 mL of anhydrous THF was added to the reaction flask via cannulation. The reaction was quenched with water and extracted with EtOAc after 2 h. The organic phase was collected, dried with sodium sulfate, filtered and concentrated under reduced pressure followed by purification by flash chromatography (silica, 50:50 EtOAc/hexane) to give 1-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-yl)ethanone. LCMS; 241.1 m/z (M+H)+.

Workup

temperatureAfter warming to rt over 1 h
customThe reaction was quenched with water
extractionextracted with EtOAc after 2 h
customThe organic phase was collected
dry with materialdried with sodium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customfollowed by purification by flash chromatography (silica, 50:50 EtOAc/hexane)

Sources & evidence

ORD record: ord-ea914fe853d74367874e191c8643a112
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445503B2

Reaction notes

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