Dimethylformamide → HCID 85772009, compound

HRID 1897614Notes

Reaction equation

HRID 1897614 reaction equation
[Li]CCCC.Br[C:7]1[CH:8]=[N:9][CH:10]=[CH:11][C:12]=1[CH:13]([O:17][CH2:18][CH3:19])[O:14][CH2:15][CH3:16].CN([CH:23]=[O:24])C>C1COCC1>[CH2:15]([O:14][CH:13]([O:17][CH2:18][CH3:19])[C:12]1[CH:11]=[CH:10][N:9]=[CH:8][C:7]=1[CH:23]=[O:24])[CH3:16]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 67155132HCID 67155132, compoundHCID 178418339Butyllithium

Product 1

HCID 85772009HCID 85772009, compoundYield 78.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

BuLi (5.84 mL, 9.35 mmol) was added to a solution of 3-bromo-4-diethoxymethyl-pyridine (2.21 g, 8.50 mmol) in THF (50 mL) at −78° C. After 1 h, DMF (6.58 mL, 85 mmol) was added. The reaction was stirred at −78° C. for 1 hr. It was then warmed to room temperature, quenched with water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated in vacuo to afford 1.4 g of 4-diethoxymethyl-pyridine-3-carbaldehyde, which was taken in the next step without further purification. MS (ESI) m/z 210.1 (M+H)+

Workup

  1. temperatureIt was then warmed to room temperature
  2. customquenched with water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0a28ebc00b9d48658f63c1820f5294ed
Source dataset
uspto-grants-2013_08
Patent number
US08519134B2

Reaction notes

Loading…