Pyridine → HCID 15723380, compound

HRID 654952Notes

Reaction equation

HRID 654952 reaction equation
[C:1]([O:4][CH:5]([C:15]1[CH:16]=[C:17]([Si:20]([CH3:23])([CH3:22])[CH3:21])[O:18][CH:19]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][OH:14])(=[O:3])[CH3:2].N1C=CC=CC=1.[C:30](Cl)(=[O:32])[CH3:31]>O1CCCC1>[C:1]([O:4][CH:5]([C:15]1[CH:16]=[C:17]([Si:20]([CH3:23])([CH3:22])[CH3:21])[O:18][CH:19]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:30](=[O:32])[CH3:31])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 15723379HCID 15723379, compound

Product 1

HCID 15723380HCID 15723380, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 4-(1-acetoxy-9-hydroxynonyl)-2-trimethylsilylfuran (0.075 g, 0.221 mmol) and pyridine (0.056 g, 0.662 mmol) in tetrahydrofuran (2 ml) under argon at 0° was added dropwise acetyl chloride (0.052 g, 0.662 mmol). The mixture was warmed to room temperature, stirred for one hour, quenched with water and extracted into ethyl ether. The organic portion was washed with 10% hydrochloric acid, saturated sodium bicarbonate, aqueous 5% cupric sulfate solution, water, saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated to an oil. Purification by flash chromatography (silica, 5 to 10% ethyl acetate/hexane) gave the desired product.

Workup

  1. customquenched with water
  2. extractionextracted into ethyl ether
  3. washThe organic portion was washed with 10% hydrochloric acid, saturated sodium bicarbonate, aqueous 5% cupric sulfate solution, water, saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to an oil
  7. customPurification by flash chromatography (silica, 5 to 10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-447c0ed11a99485c99504677fd87a9b4
Source dataset
uspto-grants-1992_07
Patent number
US05134128

Reaction notes

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