Water → [3-(Benzyloxy)propyl] iodomethyl carbonate
Reaction equation
[C:1](=[O:17])([O:14][CH2:15]Cl)[O:2][CH2:3][CH2:4][CH2:5][O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[I-:18].[Na+].O>C(#N)C>[C:1](=[O:17])([O:14][CH2:15][I:18])[O:2][CH2:3][CH2:4][CH2:5][O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
[3-(Benzyloxy)propyl] chloromethyl carbonate (2.0 g) was dissolved in acetonitrile (3 ml), and sodium iodide (4.6 g) was added. The mixture was stirred under a nitrogen atmosphere at 60° C. for 2 hours. The reaction mixture was poured into water (100 ml) and extracted with ethyl acetate (100 ml). The ethyl acetate layer was washed with an aqueous 5% sodium thiosulfate solution (50 ml×2), water (50 ml×2), and a saturated sodium chloride aqueous solution (50 ml). After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to obtain [3-(benzyloxy)propyl] iodomethyl carbonate (2.5 g) as a pale yellow liquid.
Workup
- extractionextracted with ethyl acetate (100 ml)
- washThe ethyl acetate layer was washed with an aqueous 5% sodium thiosulfate solution (50 ml×2), water (50 ml×2)
- dry with materialAfter drying over anhydrous magnesium sulfate
- distillationthe solvent was distilled off under reduced pressure
Sources & evidence
- ORD record
- ord-8569fdca70ca4403ae4ece93f3da72bf
- Source dataset
- uspto-grants-2002_06
- Patent number
- US06407129B1
Reaction notes
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