Pyridine → HCID 67083599, compound

HRID 1422555Notes

Reaction equation

HRID 1422555 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@@H:14]([CH2:15][OH:16])[O:13][CH:12]=[CH:11][C@H:10]1[OH:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:24](Cl)(=[O:26])[CH3:25]>ClCCl>[C:24]([O:16][CH2:15][C@H:14]1[O:13][CH:12]=[CH:11][C@@H:10]([OH:17])[C@@H:9]1[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)(=[O:26])[CH3:25]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 27347274-O-Benzyl-D-glucal

Product 1

HCID 67083599HCID 67083599, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

4-O-benzyl-D-glucal (21.2 mmol) and pyridine (45 mmol), were dissolved in dichloromethane (100 mL). Obtained solution was cooled down to 0° C., and acetyl chloride (25 mmol) was added. The mixture was stirred at 0° C. After reaction was completed, the reaction mixture was washed with water (3×50 mL), dried over anhydrous sodium sulfate. Drying agent and solvent were removed and product was purified by column chromatography (Silicagel 60) using hexanes:ethyl acetate as eluents. Yield 50%.

Workup

  1. customAfter reaction
  2. washthe reaction mixture was washed with water (3×50 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. customDrying agent and solvent
  5. customwere removed
  6. customproduct was purified by column chromatography (Silicagel 60)

Sources & evidence

ORD record
ord-969e5f7d396b4ea1a2f4b12cb0e47f5e
Source dataset
uspto-grants-2015_01
Patent number
US08927506B2

Reaction notes

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