3-Pyridinecarboxaldehyde → HCID 53866777, compound

HRID 1680028Notes

Reaction equation

HRID 1680028 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.C([Li])CCC.[CH:14]([C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)=[O:15].[CH2:22]([O:24][C:25](=[O:29])[CH:26](Br)[CH3:27])[CH3:23].[Cl-].[NH4+]>O1CCCC1.CCCCCC>[CH2:22]([O:24][C:25](=[O:29])[CH:26]([S:8][C:5]1[CH:6]=[CH:7][C:2]([CH:14]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[OH:15])=[CH:3][CH:4]=1)[CH3:27])[CH3:23]

Participants

8

Reactant 5

HCID 103713-PyridinecarboxaldehydeHCID 25517Ammonium ChlorideHCID 660494-BromothiophenolHCID 79040Ethyl 2-bromopropionateHCID 178418339Butyllithium

Product 1

HCID 53866777HCID 53866777, compoundYield 44.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 0.95 g of 4-bromothiophenol in 20 ml of tetrahydrofuran was added dropwise to 7.5 ml of a 1.4 M solution of butyllithium in hexane at -70° to -60° C. After allowed to warm to 0° C., the mixture was stirred at 0° C. for 5 minutes. To it was added a solution of 0.505 g of 3-formylpyridine in 10 ml of tetrahydrofuran at -70° C., and the mixture was stirred at -70° C. for 30 minutes. To the mixture was added 0.91 g of 2-bromopropionic acid ethyl ester at -70° C., and the mixture was stirred at room temperature for one hour. The reaction mixture was poured into a saturated aqueous solution of ammonium chloride, extracted with diethyl ether, and the extract was washed with a saturated aqueous solution of sodium chloride, dried over sodium sulphate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using a mixture of cyclohexane and ethyl acetate (1:4) as eluent to give 0.66 g of the title compound having the following physical characteristic:

Workup

  1. stirringthe mixture was stirred at -70° C. for 30 minutes
  2. stirringthe mixture was stirred at room temperature for one hour
  3. extractionextracted with diethyl ether
  4. washthe extract was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel using
  8. additiona mixture of cyclohexane and ethyl acetate (1:4) as eluent

Sources & evidence

ORD record
ord-31ec28c802bd457e9f9ddda5c1621068
Source dataset
uspto-grants-1981_06
Patent number
US04271170

Reaction notes

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