Acetic Anhydride → 2-Acetoxymethyl-6-butoxypyridine

HRID 1587692Notes

Reaction equation

HRID 1587692 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].[CH2:8]([O:12][C:13]1[CH:14]=[CH:15][CH:16]=C(C)[N+:18]=1[O-])[CH2:9][CH2:10][CH3:11]>C(O)(=O)C>[C:5]([O:4][CH2:1][C:2]1[CH:16]=[CH:15][CH:14]=[C:13]([O:12][CH2:8][CH2:9][CH2:10][CH3:11])[N:18]=1)(=[O:7])[CH3:6]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 678527606-butoxy-alpha-picoline N-oxide

Product 1

HCID 197561112-Acetoxymethyl-6-butoxypyridineYield 35.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
135 °C

Procedure

An amount 60 ml of acetic anhydride was stirred at about 120° C., and a solution of 11.1 g of 6-butoxy-α-picoline N-oxide in 25 ml of glacial acetic acid was dropwise added thereto over about one hour. After the dropwise addition, the mixture was stirred at 135° C. for 4.5 hours, acetic acid and acetic anhydride were removed by concentration under a reduced pressure, the reaction mixture was dissolved in ether, and the remaining acetic acid was neutralized with an aqueous sodium hydrogen carbonate solution. The mixture was extracted with ether, concentrated under a reduced pressure, and separated by silica gel column chromatography (ethyl acetate:hexane=8:92) to obtain 4.89 g of the desired product (yield 35.9%).

Workup

  1. additionAfter the dropwise addition
  2. customacetic acid and acetic anhydride were removed by concentration under a reduced pressure
  3. dissolutionthe reaction mixture was dissolved in ether
  4. extractionThe mixture was extracted with ether
  5. concentrationconcentrated under a reduced pressure
  6. customseparated by silica gel column chromatography (ethyl acetate:hexane=8:92)

Sources & evidence

ORD record
ord-4c81fc38ee994c5d86c946525f6d1703
Source dataset
uspto-grants-1993_06
Patent number
US05219847

Reaction notes

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