m-Chloroperbenzoic acid → 1,1-Dimethylethyl 6-[(acetyloxy)methyl]-3-pyridinecarboxylate

HRID 868353Notes

Reaction equation

HRID 868353 reaction equation
[CH3:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[CH:4][N:3]=1.ClC1C=CC=[C:18]([C:22]([O:24]O)=[O:23])C=1>ClCCl>[C:22]([O:24][CH2:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:11])([CH3:10])[CH3:12])=[O:7])=[CH:4][N:3]=1)(=[O:23])[CH3:18]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 21287969HCID 21287969, compound

Product 1

HCID 545296931,1-Dimethylethyl 6-[(acetyloxy)methyl]-3-pyridinecarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7.1 g of t-butyl 6-methylnicotinate in 100 ml of dichloromethane, 9.8 g of m-chloroperbenzoic acid is added slowly, and the mixture is stirred at room temperature for 1 hour. The reaction mixture is washed successively with 10% sodium carbonate solution and water, dried over magnesium sulfate, and concentrated. The residue is slowly added to 7.1 g of acetic anhydride at 100°-120° C., and the mixture is refluxed with stirring for 1 hour. After cooling, the remaining acetic anhydride is decomposed with ethanol, and the mixture is concentrated. The residue is neutralized with saturated aqueous potassium bicarbonate and extracted with three 50-ml portions of chloroform. The combined extracts are dried over magnesium sulfate and concentrated to give crude 5-t-butoxycarbonyl-2-pyridylmethanol acetate.

Workup

  1. washThe reaction mixture is washed successively with 10% sodium carbonate solution and water
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. additionThe residue is slowly added to 7.1 g of acetic anhydride at 100°-120° C.
  5. temperaturethe mixture is refluxed
  6. stirringwith stirring for 1 hour
  7. temperatureAfter cooling
  8. concentrationthe mixture is concentrated
  9. extractionextracted with three 50-ml portions of chloroform
  10. dry with materialThe combined extracts are dried over magnesium sulfate
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-2e1ec83a174c44e1b4900822ee623ac2
Source dataset
uspto-grants-1988_10
Patent number
US04778796

Reaction notes

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