Acetic Anhydride → (4-(3-Methoxypropoxy)-3-methylpyridin-2-yl)methyl acetate
Reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][N+:10]([O-])=[C:9]([CH3:14])[C:8]=1[CH3:15].[C:16]([O:19]C(=O)C)(=[O:18])[CH3:17]>>[C:16]([O:19][CH2:14][C:9]1[C:8]([CH3:15])=[C:7]([O:6][CH2:5][CH2:4][CH2:3][O:2][CH3:1])[CH:12]=[CH:11][N:10]=1)(=[O:18])[CH3:17]Participants
Procedure
20 ml of acetic anhydride was added to 760 mg (3.6 mmol) of 4-(3-methoxypropoxy)-2,3-dimethyl-pyridine N-oxide to carry out the reaction at 90° C. for one hour. The reaction mixture was distilled to remove the acetic anhydride, followed by the addition of a saturated aqueous solution of sodium hydrogen-carbonate. The obtained mixture was extracted with chloroform. The extract was concentrated to obtain 700 mg of 2-acetoxymethyl-4-(3-methoxypropoxy)-3-methylpyridine as a brown oil. 500 mg of sodium hydroxide and 15 cc of ethanol were added to the 2-acetoxymethyl-4-(3-methoxypropoxy)-3-methylpyridine prepared above. The obtained mixture was stirred at 50° C. for one hour. After the completion of the reaction, the reaction mixture was distilled to remove the ethanol, followed by the addition of water. The obtained mixture was extracted with chloroform. The obtained chloroform layer was concentrated to obtain 450 mg of 2-hydroxymethyl-4-(3-methoxypropoxy)-3-methylpyridine as a brown oil.
Workup
- customthe reaction at 90° C. for one hour
- distillationThe reaction mixture was distilled
- customto remove the acetic anhydride
- additionfollowed by the addition of a saturated aqueous solution of sodium hydrogen-carbonate
- extractionThe obtained mixture was extracted with chloroform
- concentrationThe extract was concentrated
Sources & evidence
- ORD record
- ord-f3cb4e8f863847d4bfd08e36a4b0e29f
- Source dataset
- uspto-grants-1999_12
- Patent number
- US05998445
Reaction notes
Loading…