(1R)-3-chloro-1-phenylpropan-1-ol → (R)-3-phthalimido-1-phenylpropanol
Reaction equation
Cl[CH2:2][CH2:3][C@H:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[OH:5].[C:12]1(=[O:22])[NH:16][C:15](=[O:17])[C:14]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:13]12.[K]>CN(C)C=O>[C:12]1(=[O:22])[N:16]([CH2:2][CH2:3][C@H:4]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[OH:5])[C:15](=[O:17])[C:14]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:13]12Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
To a solution of 10.09 g of (R)-(+)-3-chloro-1-phenylpropanol in 80 ml of dimethylformamide were added 13.14 g of potassium phthalimide in 80 ml of dimethylformamide. The mixture was heated at 100° C. for 8 hours, allowed to cool to room temperature, and filtered. The filtrate was diluted with water, and the solution extracted 3 times with ethyl acetate. The combined organic extracts were washed once with water, once with 0.2 N sodium hydroxide, once again with water, and once with a saturated solution of sodium chloride, dried over sodium sulfate, and concentrated in vacuo to provide an opaque oil that solidified. Crystallization from ethyl acetate/hexanes provided 11.09 g of the title intermediate as clear pale yellow needles, m.p. 81°-83° C.
Workup
- temperatureto cool to room temperature
- filtrationfiltered
- additionThe filtrate was diluted with water
- extractionthe solution extracted 3 times with ethyl acetate
- washThe combined organic extracts were washed once with water, once with 0.2 N sodium hydroxide, once again with water
- dry with materialonce with a saturated solution of sodium chloride, dried over sodium sulfate
- concentrationconcentrated in vacuo
- customto provide an opaque oil that solidified
- customCrystallization from ethyl acetate/hexanes
Sources & evidence
- ORD record
- ord-c75d82fe173e4749a6c63cf296f9f187
- Source dataset
- uspto-grants-1993_10
- Patent number
- US05250572
Reaction notes
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