Propanal → HCID 21912322, compound

HRID 1760691Notes

Reaction equation

HRID 1760691 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([O:9][C:10]2[C:15]([CH3:16])=[CH:14][C:13]([CH3:17])=[CH:12][C:11]=2[CH3:18])[C:3]=1[CH3:19].[CH:20](=[O:23])[CH2:21][CH3:22]>C1COCC1>[CH3:19][C:3]1[C:4]([O:9][C:10]2[C:15]([CH3:16])=[CH:14][C:13]([CH3:17])=[CH:12][C:11]=2[CH3:18])=[N:5][C:6]([CH3:8])=[CH:7][C:2]=1[CH:20]([OH:23])[CH2:21][CH3:22]

Participants

4

Reactant 2

HCID 527PropanalHCID 21912337HCID 21912337, compound

Product 1

HCID 21912322HCID 21912322, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a −78° C. solution of 4-bromo-3,6-dimethyl-2-(2,4,6-trimethyl-phenoxy)pyridine in dry THF was added nBuli and stirred at that temperature for 20 minutes. Excess propionaldehyde was added and stirred for 2 hours at −78° C. The mixture was quenched with water, extracted with ethyl acetate. The organic layer was washed with brine, dried and concentrated. After column chromatography, an off-white solid was obtained, mp. 119-120° C. 1H NMR(CDCl3) d 6.86(s,3H), 4.90(m,1H), 2.281(s,3H), 2.28(s,3H), 2.21(s,3H), 2.02(s,6H), 1.65-1.8(m,2H), 1.00(t,3H) ppm.

Workup

  1. stirringstirred for 2 hours at −78° C
  2. customThe mixture was quenched with water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. customdried
  6. concentrationconcentrated
  7. customAfter column chromatography, an off-white solid was obtained

Sources & evidence

ORD record
ord-f4e2517378c04eb28709e97231a43dcd
Source dataset
uspto-grants-2005_01
Patent number
US06844351B1

Reaction notes

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