Acetone → (3-(Benzyloxy)pyridin-2-yl)methanol
Reaction equation
[OH-].[Na+].CC(C)=O.Cl.[OH:8][C:9]1[C:10]([CH2:15][OH:16])=[N:11][CH:12]=[CH:13][CH:14]=1.[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O>[CH2:17]([O:8][C:9]1[C:10]([CH2:15][OH:16])=[N:11][CH:12]=[CH:13][CH:14]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1Participants
Procedure
Sodium hydroxide (31.5 grams, 0.78 mole) was dissolved in 100 ml water and 100 ml of acetone was added followed by 3-hydroxy-2(hydroxymethyl)pyridine hydrochloride (63.8 grams; 0.39 mole). 250 ml of acetone was added followed by benzyl bromide (74.1 grams; 51.5 ml; 0.43 mole). The mixture was refluxed for a period of 4.5 hours and the acetone evaporated in vacuo. The aqueous layer was extracted with CH2Cl2 (three times 150 ml) and the extracts dried (anhydrous Na2SO4) and concentrated to yield 88.1 grams of a brown liquid. The brown liquid (88.1 grams) was dissolved in ether and ether-HCl added to form the hydrochloride salt. The HCl salt was filtered and the filter cake dissolved in water. The aqueous solution was basified to afford a brown pasty precipate which on trituration with ether afforded 58.7 grams of material. Recrystallization from ethanol yielded 31.6 grams of a tan solid, m.p. 79°-80° C.
Workup
- temperatureThe mixture was refluxed for a period of 4.5 hours
- customthe acetone evaporated in vacuo
- extractionThe aqueous layer was extracted with CH2Cl2 (three times 150 ml)
- dry with materialthe extracts dried (anhydrous Na2SO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-320bf9524af545fd81f3ebb3ca2584f0
- Source dataset
- uspto-grants-1984_10
- Patent number
- US04478834
Reaction notes
Loading…