Pyridine → HCID 19885889, compound

HRID 654921Notes

Reaction equation

HRID 654921 reaction equation
[OH:1][CH2:2][C:3]1[CH:7]=[CH:6][O:5][CH:4]=1.N1C=CC=CC=1.[C:14](Cl)(=[O:26])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]>O1CCCC1>[C:14]([O:1][CH2:2][C:3]1[CH:7]=[CH:6][O:5][CH:4]=1)(=[O:26])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

5

Reactant 3

HCID 1049PyridineHCID 8166Dodecanoyl chlorideHCID 204493-Furanmethanol

Product 1

HCID 19885889HCID 19885889, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3-hydroxymethylfuran (1.01 g., 10.3 mmol) and pyridine (0.87 g., 10.3 mmol) in 30 ml dry tetrahydrofuran at 0° under argon was added lauroyl chloride (2.36 g., 10.8 mmol). This solution was allowed to warm to room temperature, during which time a white precipitate formed. After one hour, the mixture was filtered and the solution partitioned between ethyl ether and a 5% ammonium chloride solution. The organic portion was washed twice with 5% sodium bicarbonate solution, three times with aqueous cupric sulfate solution, water, saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated to give a yellow oil. This material was further purified by flash chromatography (silica, 5% ethyl ether/petroleum ether) to give the desired ester.

Workup

  1. customformed
  2. filtrationthe mixture was filtered
  3. customthe solution partitioned between ethyl ether
  4. washThe organic portion was washed twice with 5% sodium bicarbonate solution, three times with aqueous cupric sulfate solution, water, saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a yellow oil
  9. customThis material was further purified by flash chromatography (silica, 5% ethyl ether/petroleum ether)

Sources & evidence

ORD record
ord-0e790b55774a45a6b5b2f42dcc33b276
Source dataset
uspto-grants-1992_07
Patent number
US05134128

Reaction notes

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