Dimethylformamide → HCID 23103619, compound

HRID 2116485Notes

Reaction equation

[CH3:1][Si:2]([CH3:15])([CH3:14])[CH2:3][CH2:4][O:5][CH2:6][O:7][C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1.CCCCC.C([Li])(C)(C)C.CN(C)[CH:28]=[O:29].[Cl-].[NH4+]>O1CCCC1>[CH:28]([C:13]1[CH:12]=[CH:11][N:10]=[CH:9][C:8]=1[O:7][CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:15])([CH3:14])[CH3:1])=[O:29]

Participants

Conditions

Temperature: -70 °C

Procedure

To a solution of 3-[2-(trimethylsilyl)ethoxymethoxy]pyridine (39.3 g, 0.174 mol) in tetrahydrofuran (250 ml), a 1.47 mol/L t-butyllithium n-pentane solution (154 ml, 0.227 mol) was added dropwise at −70° C. over 40 minutes. After stirring at −70° C. for 1 hour, N,N-dimethylformamide (40 mL, 0.522 mol) was added over 30 minutes and stirred at −70° C. for 1.5 hours. After warming to −20° C., saturated aqueous ammonium chloride was added to the reaction mixture, which was then extracted twice with ethyl acetate. The organic layers were dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=80:20) to give 4-formyl-3-[2-(trimethylsilyl)ethoxymethoxy]pyridine (24.5 g, 58%) as a brown oil.

Workup

stirringstirred at −70° C. for 1.5 hours
temperatureAfter warming to −20° C.
extractionwas then extracted twice with ethyl acetate
dry with materialThe organic layers were dried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=80:20)

Sources & evidence

ORD record: ord-52ca5c644b6e446abf87739945d56905
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07439232B2

Reaction notes

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