Acetonitrile → HCID 58416506, compound

HRID 1014995Notes

Reaction equation

Cl[C:2]1[C:7]([C:8]2([CH3:13])[O:12][CH2:11][CH2:10][O:9]2)=[CH:6][CH:5]=[CH:4][N:3]=1.[C:14](#[N:16])[CH3:15].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[NH4+].[Cl-]>C1COCC1>[CH3:13][C:8]1([C:7]2[C:2]([CH2:15][C:14]#[N:16])=[N:3][CH:4]=[CH:5][CH:6]=2)[O:12][CH2:11][CH2:10][O:9]1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 2-chloro-3-(2-methyl-[1,3]dioxolan-2-yl)-pyridine (2.19 g, 11.0 mmol, 1.0 equiv) and acetonitrile (577 μL, 11.0 mmol, 1.0 equiv) in THF (75 mL) is cooled to 5° C. under nitrogen atmosphere. 2M Sodium bis(trimethylsilyl)amide solution in THF (11.0 mL, 21.9 mmol, 2.0 equiv) is added within 1 minute. This results in a bright yellow solution which turns orange over time. Stirring at 0° C. is continued for exact 1 h. According to TLC there is complete conversion. Saturated NH4Cl solution (50 mL) is added. The organic layer is separated and concentrated in vacuo. The residue is combined with the water layer and extracted with ethyl acetate (75 mL). The organic layer is washed three times with sat. NH4Cl solution, dried over Na2SO4 and evaporated in vacuo. The residue is purified by flash column chromatography (10% to 50% ethyl acetate in heptane) and gave 540 mg of the title compound as an oil.

Workup

customThis results in a bright yellow solution which
customThe organic layer is separated
concentrationconcentrated in vacuo
extractionextracted with ethyl acetate (75 mL)
washThe organic layer is washed three times with sat. NH4Cl solution
dry with materialdried over Na2SO4
customevaporated in vacuo
customThe residue is purified by flash column chromatography (10% to 50% ethyl acetate in heptane)

Sources & evidence

ORD record: ord-ad1a29dd34574242b721d6330267458c
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07985753B2

Reaction notes

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