Propanal → HCID 21912322, compound

HRID 1831688Notes

Reaction equation

HRID 1831688 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].[Li]CCCC.[CH:25](=[O:28])[CH2:26][CH3:27]>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:25]([OH:28])[CH2:26][CH3:27]

Participants

5

Reactant 3

HCID 527PropanalHCID 21912337HCID 21912337, compoundHCID 178418339Butyllithium

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-43948da099bb4919832f929c8d603a50
Source dataset
uspto-grants-2006_06
Patent number
US07067664B1

Reaction notes

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