Triethylamine → Oxetan-3-ylmethyl methanesulfonate
Reaction equation
[O:1]1[CH2:4][CH:3]([CH2:5][OH:6])[CH2:2]1.C(N(CC)CC)C.[CH3:14][S:15](Cl)(=[O:17])=[O:16]>C(Cl)Cl>[CH3:14][S:15]([O:6][CH2:5][CH:3]1[CH2:4][O:1][CH2:2]1)(=[O:17])=[O:16]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Oxetan-3-ylmethanol (1.85 g, 21.0 mmol) was dissolved in methylene chloride and cooled to 0° C. Triethylamine (5.31 g, 52.2 mmol) was added followed by slow addition of methanesulfonyl chloride (2.89 g, 25.2 mmol). The mixture was allowed to warm to ambient temperature for 2 h and quenched with sat. sodium bicarbonate (14 mL). The aqueous solution was extracted with methylene chloride 3×. The combined organic layers were dried over sodium sulfate, filtered and concentrated to give crude oxetan-3-ylmethyl methanesulfonate (quant.).
Workup
- temperatureto warm to ambient temperature for 2 h
- customquenched with sat. sodium bicarbonate (14 mL)
- extractionThe aqueous solution was extracted with methylene chloride 3×
- dry with materialThe combined organic layers were dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-3452a4ced46a404d9ad0478512be16b4
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08614206B2
Reaction notes
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