Ethyl Acetate → HCID 59278652, compound

HRID 242163Notes

Reaction equation

HRID 242163 reaction equation
C[C:2](C)([O-:4])C.[K+].Cl[C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][N:9]=1.[C:16]([O:19][CH2:20][CH3:21])(=[O:18])[CH3:17].[C:22](=O)(O)[O-].[Na+]>CN(C=O)C>[CH3:17][C:16]1([CH3:22])[O:18][C@H:21]([CH2:2][O:4][C:8]2[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][N:9]=2)[CH2:20][O:19]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 27640536-Chloropyridine-3-carbaldehydeHCID 23665647Potassium tert-butoxide

Product 1

HCID 59278652HCID 59278652, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7.47 g (56.51 mmol) of R-(−)-2,3-dimethyl-1,3-dioxolane-4-methanol are initially charged in 80 ml of dry DMF, and 4.76 g (42.39 mmol) of potassium tert-butoxide are added. The mixture is stirred at RT for 15 min 4.00 g (28.26 mmol) of 6-chloronicotinaldehyde are then added. The reaction mixture is stirred at RT for 12 h. The mixture is then poured into a mixture of 100 ml of ethyl acetate and 100 ml of aq. sodium bicarbonate solution. The phases are separated, and the organic phase is washed twice with in each case 30 ml of water. The organic phase is dried over magnesium sulphate, and the solvent is removed on a rotary evaporator. The residue is purified by column chromatography on silica gel 60 (mobile phase gradient: cyclohexane/ethyl acetate 50:1→2:1). Without further purification, the product obtained in this manner is used for the subsequent step.

Workup

  1. additionare then added
  2. customThe phases are separated
  3. washthe organic phase is washed twice with in each case 30 ml of water
  4. dry with materialThe organic phase is dried over magnesium sulphate
  5. customthe solvent is removed on a rotary evaporator
  6. customThe residue is purified by column chromatography on silica gel 60 (mobile phase gradient: cyclohexane/ethyl acetate 50:1→2:1)
  7. customWithout further purification
  8. customthe product obtained in this manner

Sources & evidence

ORD record
ord-75f060a3079749bf910a392fe255d2fc
Source dataset
uspto-grants-2014_02
Patent number
US08653109B2

Reaction notes

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