Sodium Iodide → (R)-3-iodo-1-phenyl-1-propanol
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].[I-:12].[Na+]>CC(C)=O>[I:12][CH2:2][CH2:3][C@H:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[OH:5]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of (R)-(+)-3-chloro-1-phenyl-1-propanol (5 g, 29.3 mmol) in acetone (50 mL) was added sodium iodide (4.83 g, 32.2 mmol). The resulting solution was heated at reflux for 16 h. The solution was cooled, filtered and concentrated in vacuo. The residue was purified by flash chromatography eluting silica gel with hexane:ethyl acetate [100:0 to 3:1] to yield the title compound as a white solid (7.51 g, 98%); δH (300 MHz, CDCl3) 7.36 (5H, m, Ar), 4.83 (1H, m, O—CH), 3.34–3.15 (2H, m, CH2), 2.28–2.15 (2H, m, CH2).
Workup
- temperatureThe resulting solution was heated
- temperatureat reflux for 16 h
- temperatureThe solution was cooled
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue was purified by flash chromatography
- washeluting silica gel with hexane
Sources & evidence
- ORD record
- ord-6f4743f794d84e83935a1ab25a2e56f0
- Source dataset
- uspto-grants-2006_05
- Patent number
- US07037932B2
Reaction notes
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