Pyridine → HCID 23368802, compound

HRID 1901774Notes

Reaction equation

HRID 1901774 reaction equation
[OH:1][CH:2]([CH2:5][O:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][O:8]1)[C:3]#[CH:4].[C:13](OC(=O)C)(=[O:15])[CH3:14].N1C=CC=CC=1>>[C:13]([O:1][CH:2]([CH2:5][O:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][O:8]1)[C:3]#[CH:4])(=[O:15])[CH3:14]

Participants

4

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 18920430HCID 18920430, compound

Product 1

HCID 23368802HCID 23368802, compoundYield 90.2%

Procedure

3-Hydroxy-4-(tetrahydro-2-pyranyloxy)-butyne (8.0 g, 0.047 mole) was mixed with acetic anhydride (10 g, 0.098 mole) and pyridine (8 g, 0.098 mole). The solution was stirred at room temperature for 1 hour and then extracted with ethyl acetate. The extract was sequentially washed with 10% hydrochloric acid (10 ml×5), saturated sodium bicarbonate aqueous solution (10 ml×5) and water (50 ml×3). The extract was dried over anhydrous magnesium sulfate, concentrated and separated by silica gel chromatography, eluted with n-hexane/ethyl acetate (5:1) to give colorless oil (9.0 g, 90%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was sequentially washed with 10% hydrochloric acid (10 ml×5), saturated sodium bicarbonate aqueous solution (10 ml×5) and water (50 ml×3)
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customseparated by silica gel chromatography
  6. washeluted with n-hexane/ethyl acetate (5:1)

Sources & evidence

ORD record
ord-c1a27de7168b4f11bf5336d24f84fa03
Source dataset
uspto-grants-1996_11
Patent number
US05578636

Reaction notes

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