Ethyl acetate hexane → 1-(3-(Methoxymethoxy)-6-neopentylpyridin-2-yl)ethanone

HRID 1697201Notes

Reaction equation

COC[O:4][C:5]1[C:6](C#N)=[N:7][C:8]([CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:9][CH:10]=1.C[Mg]Cl.[CH3:21][CH2:22][O:23][C:24](C)=[O:25].[CH3:27]CCCCC>C1COCC1>[CH3:27][O:25][CH2:24][O:23][C:22]1[C:6]([C:5](=[O:4])[CH3:10])=[N:7][C:8]([CH2:11][C:12]([CH3:14])([CH3:13])[CH3:15])=[CH:9][CH:21]=1

Participants

Conditions

Temperature: 0 °C

Procedure

3-(Methoxymethoxy)-6-neopentylpicolinonitrile (8.3 g, 35 mmol) was dissolved in THF (125 mL). The solution was cooled to 0° C. and methylmagnesium chloride (24 ml, 71 mmol) (3.0 M in Et2O) was added. The reaction mixture stirred for 2 h at rt under N2 then quenched with saturated NH4Cl (50 mL) and extracted with EtOAc (3×50 mL). The organic layer was dried over MgSO4 and evaporated to give the crude product as a yellow oil. Purification of the crude residue by ISCO (40 g SiO2, O-40% EtOAc/Hexane) gave 1-(3-(methoxymethoxy)-6-neopentylpyridin-2-yl)ethanone (3.8 g, 43% yield) as a clear, light orange oil.

Workup

customthen quenched with saturated NH4Cl (50 mL)
extractionextracted with EtOAc (3×50 mL)
dry with materialThe organic layer was dried over MgSO4
customevaporated
customto give the crude product as a yellow oil
customPurification of the crude residue by ISCO (40 g SiO2

Sources & evidence

ORD record: ord-c10158cb40194f35aa9492d5bd2f2824
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163909B2

Reaction notes

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