4-Pyridinecarboxaldehyde → HCID 21249892, compound

HRID 1956541Notes

Reaction equation

HRID 1956541 reaction equation
[Br-].[CH3:2][C:3]([CH3:11])=[CH:4][CH2:5][S+]1CCCC1.[N:12]1[CH:17]=[CH:16][C:15]([CH:18]=[O:19])=[CH:14][CH:13]=1.[H-].[Na+]>>[CH3:11][C:3]([CH3:2])=[CH:4][CH:5]1[O:19][CH:18]1[C:15]1[CH:16]=[CH:17][N:12]=[CH:13][CH:14]=1

Participants

4

Reactant 3

HCID 133894-Pyridinecarboxaldehyde2×HCID 24758Sodium hydrideHCID 21249890HCID 21249890, compound

Product 1

HCID 21249892HCID 21249892, compound

Procedure

To a suspension of 1-(3-methyl-but-2-enyl)-tetrahydrothiophenium bromide (381 mg in 5 mL dry tetrahydrofuran) at 0° C. was added 0.31 mL pyridine-4-carboxaldehyde followed by 111 mg sodium hydride and the mixture allowed to warm to room temperature. After 1.5 hours, an additional 0.15 mL pyridine-4-carboxaldehyde was added and after 30 minutes the reaction quenched by the addition of water. The mixture was partitioned between ethyl acetate and water and the organic portion washed with saturated aqueous sodium bicarbonate and dried over sodium sulfate. Purification of the concentrate by flash chromatography on silica gel (hexane:ethyl acetate, 1:2) gave the title compound (138 mg). Step 4C

Workup

  1. customquenched by the addition of water
  2. customThe mixture was partitioned between ethyl acetate and water
  3. washthe organic portion washed with saturated aqueous sodium bicarbonate
  4. dry with materialdried over sodium sulfate
  5. customPurification of the
  6. concentrationconcentrate by flash chromatography on silica gel (hexane:ethyl acetate, 1:2)

Sources & evidence

ORD record
ord-3ee260b9f7f9422ea2e9de80102e72b1
Source dataset
uspto-grants-1998_07
Patent number
US05780437

Reaction notes

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