Acetic Anhydride → 1,3-Dioxolo[4,5-C]pyridine-4-methanol

HRID 1647171Notes

Reaction equation

HRID 1647171 reaction equation
[CH3:1][C:2]1[C:7]2[O:8][CH2:9][O:10][C:6]=2[CH:5]=[CH:4][N+:3]=1[O-].C(OC(=O)C)(=[O:14])C>>[OH:14][CH2:1][C:2]1[C:7]2[O:8][CH2:9][O:10][C:6]=2[CH:5]=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 199264794-Methyl-5-oxido-[1,3]dioxolo[4,5-c]pyridin-5-ium

Product 1

HCID 199264631,3-Dioxolo[4,5-C]pyridine-4-methanol

Conditions

Temperature
110 °C

Procedure

2-Methyl-3,4-methylenedioxypyridine-N-oxide (120 mg, 0.78 mmol) was dissolved in acetic anhydride (10 ml) and the solution was heated at 110° C. for 15 min, whereupon the mixture was concentrated under reduced pressure. The residue was dissolved in methanol (20 ml) and sodium hydroxide (3 drops, 6M) was added. After 30 min at ambient temperature the mixture was neutralised with acetic acid (pH 6) and concentrated under reduced pressure. The residue was chromatographed on silica (hexane/ethyl acetate, 1:1). Yield: 90 mg (75%) of the title compound.

Workup

  1. concentrationwas concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in methanol (20 ml)
  3. additionsodium hydroxide (3 drops, 6M) was added
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was chromatographed on silica (hexane/ethyl acetate, 1:1)

Sources & evidence

ORD record
ord-28f7757c3aa948fe8410877b4c17c695
Source dataset
uspto-grants-1995_07
Patent number
US05430042

Reaction notes

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