Dimethylformamide → 5-(1,3-Dioxolan-2-yl)picolinaldehyde

HRID 1694109Notes

Reaction equation

[O:1]1CCC[CH2:2]1.Br[C:7]1[CH:12]=[CH:11][C:10]([CH:13]2[O:17][CH2:16][CH2:15][O:14]2)=[CH:9][N:8]=1.C([Li])CCC.CN(C)C=O>O>[O:14]1[CH2:15][CH2:16][O:17][CH:13]1[C:10]1[CH:11]=[CH:12][C:7]([CH:2]=[O:1])=[N:8][CH:9]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a tetrahydrofuran (100 mL) solution of 2-bromo-5-[1,3]dioxolan-2-yl-pyridine (4.77 g, 20.7 mmol) described in Manufacturing Example 154-1-2 was added n-butyl lithium (14.3 mL, 1.6 M hexane solution, 22.8 mmol) under nitrogen atmosphere at −78° C., which was stirred for 20 minutes at −78° C. Then, N,N-dimethylformamide (1.92 mL, 24.8 mmol) was added to the reaction mixture, which was stirred for 15 minutes while the temperature was raised to room temperature. Water was added to the reaction mixture at room temperature, which was extracted with ethyl acetate. The organic layer was separated, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue was purified by silica gel column chromatography (heptane:ethyl acetate=2:1) to obtain the title compound (1.73 g, 47%).

Workup

stirringwas stirred for 15 minutes while the temperature
temperaturewas raised to room temperature
extractionwhich was extracted with ethyl acetate
customThe organic layer was separated
washwashed with saturated aqueous sodium chloride
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
concentrationThe filtrate was concentrated under a reduced pressure
customthe residue was purified by silica gel column chromatography (heptane:ethyl acetate=2:1)

Sources & evidence

ORD record: ord-7e708bfd51d64114999fc85ee7faa32e
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08158657B2

Reaction notes

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