2-Thiophenecarboxaldehyde → HCID 23284530, compound

HRID 368975Notes

Reaction equation

HRID 368975 reaction equation
C([Li])CCC.C(NC(C)C)(C)C.[Cl:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1.[S:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[CH:25]=[O:26]>[Cl-].[Na+].O.O1CCCC1.CCCCCC>[Cl:13][C:14]1[C:19]([CH:25]([C:21]2[S:20][CH:24]=[CH:23][CH:22]=2)[OH:26])=[CH:18][CH:17]=[CH:16][N:15]=1

Participants

8

Reactant 4

HCID 73642-ThiophenecarboxaldehydeHCID 7912DiisopropylamineHCID 79772-ChloropyridineHCID 178418339Butyllithium

Product 1

HCID 23284530HCID 23284530, compoundYield 59%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
-78 °C

Procedure

Under an atmosphere of argon, 1.6 M hexane (30 ml) solution of n-butyl lithium was added dropwise to a tetrahydrofuran (200 ml) solution of diisopropylamine (5.52 g, 54.7 mmol) which was cooled at -78° C., and the mixture was stirred for 30 minutes 2-Chloropyridine (5.71 g, 50.3 mmol) was added dropwise to the reaction solution, followed by 90 minutes of stirring. 2-Thiophenecarbaldehyde (6.01 g, 53.7 mmol) was added dropwise to the reaction solution, followed by 30 minutes of stirring. The reaction solution was mixed with brine and extracted with chloroform. The organic layer was washed with brine and dried over anhydrous sodium sulfate. After removing sodium sulfate by filtration, the solvent was evaporated under a reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform) to give α-(2-chloropyridin-3-yl)-2-thiophenmethanol (6.66 g, 27.5 mmol, 59%).

Workup

  1. additionwas added dropwise to the reaction solution
  2. waitfollowed by 30 minutes
  3. stirringof stirring
  4. extractionextracted with chloroform
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customAfter removing sodium sulfate
  8. filtrationby filtration
  9. customthe solvent was evaporated under a reduced pressure
  10. customthe resulting residue was purified by silica gel column chromatography (chloroform)

Sources & evidence

ORD record
ord-6ff4f3e68e224a489e2df72dd2fd3b11
Source dataset
uspto-grants-2000_10
Patent number
US06136810

Reaction notes

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