Triethylamine → (2R)-1,4-dioxan-2-ylmethyl methanesulfonate
Reaction equation
[O:1]1[CH2:6][CH2:5][O:4][CH2:3][C@@H:2]1[CH2:7][OH:8].C(N(CC)CC)C.[CH3:16][S:17](Cl)(=[O:19])=[O:18]>ClCCl>[CH3:16][S:17]([O:8][CH2:7][C@H:2]1[CH2:3][O:4][CH2:5][CH2:6][O:1]1)(=[O:19])=[O:18]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -10 °C
Procedure
A round bottomed flask was charged with (2S)-1,4-dioxan-2-ylmethanol (115 mg, 0.973 mmol), triethylamine (0.204 mL, 1.46 mmol), and 5 mL of dichloromethane then cooled to −10° C. Methanesulfonyl chloride (91 μL, 1.17 mmol) was added by syringe and the solution was stirred for 30 minutes at −10° C. The solution was diluted in dichloromethane, washed with 1 M HCl, and the aqueous layer was extracted with dichloromethane (2×). The combined organic layers were washed with saturated aquoues sodium bicarbonate (2×) and brine, then dried over sodium sulfate and concentrated to afford (2R)-1,4-dioxan-2-ylmethyl methanesulfonate.
Workup
- washwashed with 1 M HCl
- extractionthe aqueous layer was extracted with dichloromethane (2×)
- washThe combined organic layers were washed with saturated aquoues sodium bicarbonate (2×) and brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-c18f343f842d47d6bff2ea7b5a867537
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07893081B2
Reaction notes
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