4-Hydroxybenzaldehyde → 4-[2-(5-Ethyl-2-pyridinyl)-2-hydroxyethoxy]benzaldehyde

HRID 2242502Notes

Reaction equation

HRID 2242502 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:17][CH:18]([C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH3:27])=[CH:22][N:21]=1)[OH:19].O>CN(C)C=O>[CH2:26]([C:23]1[CH:24]=[CH:25][C:20]([CH:18]([OH:19])[CH2:17][O:1][C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)=[N:21][CH:22]=1)[CH3:27]

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 962WaterHCID 11430Potassium CarbonateHCID 45095769HCID 45095769, compound

Product 1

HCID 115507874-[2-(5-Ethyl-2-pyridinyl)-2-hydroxyethoxy]benzaldehydeYield 68.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
85 °C

Procedure

Into a solution of 2.9 g (0.0234 mol) of 4-hydroxy benzaldehyde dissolved in 100 mL dimethylformamide, 8.94 g (0.063 mol) of potassium carbonate in 20 mL dimethylformamide was added in 10 min. followed by slow addition of 5 g (0.0213 mol) of 2-bromo-1-(5-ethyl-pyridin-2-yl)-ethanol dissolved in 1000 mL dimethylformamide. Reaction mixture was stirred for 1 hr. at 25 to 30° C., heated at 80 to 90° C. for 14 hr. and poured into excess of water at 25° C. Product was extracted with diethyl ether. Subsequent concentration in vacuo of the organic layer and purification as described earlier yielded 3.97 g (67.5%) of the desired product. m.p. 80° C.

Workup

  1. customReaction mixture
  2. extractionProduct was extracted with diethyl ether
  3. concentrationSubsequent concentration
  4. customin vacuo of the organic layer and purification

Sources & evidence

ORD record
ord-49aeb6d0f9ee43a5bb2b73bbb80294aa
Source dataset
uspto-grants-2010_03
Patent number
US07671207B2

Reaction notes

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