Dimethylformamide → HCID 86678201, compound

HRID 1747547Notes

Reaction equation

C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([CH:13]([O:17][CH2:18][CH3:19])[O:14][CH2:15][CH3:16])=[CH:9][N:8]=1.CN([CH:23]=[O:24])C.[Cl-].[NH4+]>C1(C)C=CC=CC=1.O.C1COCC1>[CH2:15]([O:14][CH:13]([O:17][CH2:18][CH3:19])[C:10]1[CH:11]=[CH:12][C:7]([CH:23]=[O:24])=[N:8][CH:9]=1)[CH3:16]

Participants

Conditions

Temperature: -78 °C

Procedure

To toluene (3 mL) were added dropwise at −78° C. n-butyllithium (2.6 mol/L solution in n-hexane, 0.94 mL, 2.43 mmol) and a solution of 2-bromo-5-(diethoxymethyl)pyridine (575 mg, 2.21 mmol) obtained in Step 1 of Reference Example 42 in toluene (2 mL), and the mixture was stirred at −78° C. for 30 minutes. THF (2 mL) was added to the resulting suspension and the mixture was stirred at −78° C. for 30 minutes. DMF (0.51 mL, 6.63 mmol) was added and the mixture was stirred for 30 minutes allowing the temperature to rise slowly to room temperature. A saturated aqueous ammonium chloride solution and water were added to the reaction mixture. Extraction with ethyl acetate, washing with saturated brine and drying over anhydrous sodium sulfate were performed. After filtration, the solvent in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1) to give 5-(diethoxymethyl)picolinaldehyde (149 mg, 32% yield).

Workup

stirringthe mixture was stirred for 30 minutes
customto rise slowly to room temperature
extractionExtraction with ethyl acetate
washwashing with saturated brine
dry with materialdrying over anhydrous sodium sulfate
filtrationAfter filtration
customthe solvent in the filtrate was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1)

Sources & evidence

ORD record: ord-eb4a9c373fe34bfaa5aa50ac4d3c3348
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150569B2

Reaction notes

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