Water → 1-Benzhydryl-3-phenoxyazetidine
Reaction equation
[NH2-].[Na+].[C:3]1([OH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH:10]([N:23]1[CH2:26][CH:25](OS(C)(=O)=O)[CH2:24]1)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O>C1(C)C=CC=CC=1>[O:9]([CH:25]1[CH2:26][N:23]([CH:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:24]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To a suspension of 8.6 g (0.22 mole) of sodium amide in 100 mL of dry toluene was added 18.8 g (0.2 mole) of phenol in 50 mL of dry toluene. The mixture was stirred at 60° C. for 2 hr. and the reaction temperature raised to 80° C. A solution of 63.4 g (0.2 mole) of 1-benzhydryl-3-methanesulfonyloxyazetidine (J. Org. Chem. 37, 3954 (1972)) in 200 ml of dry toluene was added dropwise. After stirring 2 hr at 80° C. the mixture was cooled and water added. The toluene was extracted with dilute NaOH solution, dried (Na2SO4) and concentrated. About one-third of the residue was removed. The rest of the residue was crystallized twice from water-isopropyl alcohol. Yield 9.3 g (15%); m.p. 83°-85° C.
Workup
- temperatureand the reaction temperature raised to 80° C
- stirringAfter stirring 2 hr at 80° C. the mixture
- temperaturewas cooled
- extractionThe toluene was extracted with dilute NaOH solution
- dry with materialdried (Na2SO4)
- concentrationconcentrated
- customAbout one-third of the residue was removed
- customThe rest of the residue was crystallized twice from water-isopropyl alcohol
Sources & evidence
- ORD record
- ord-f2d62e9a7c2b48fa936675032248d8d6
- Source dataset
- uspto-grants-1992_07
- Patent number
- US05130309
Reaction notes
Loading…