Triethylamine → 6-Methoxyhexahydrofuro[3,2-b]furan-3-yl methanesulfonate
Reaction equation
[CH3:1][O:2][CH:3]1[CH:7]2[O:8][CH2:9][CH:10]([OH:11])[CH:6]2[O:5][CH2:4]1.C(N(CC)CC)C.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>C(Cl)Cl>[CH3:19][S:20]([O:11][CH:10]1[CH2:9][O:8][CH:7]2[CH:3]([O:2][CH3:1])[CH2:4][O:5][CH:6]12)(=[O:22])=[O:21]Participants
5
Procedure
To a solution of 6-methoxyhexahydrofuro[3,2-b]furan-3-ol (1.03 g, 6.43 mmol) in anhydrous DCM (30 mL) were added N,N-diethylethanamine (1.3 mL, 9.4 mmol) and methanesulfonyl chloride (0.58 mL, 7.5 mmol). The reaction was stirred at rt for 6 h. The reaction was quenched with NaHCO3 (sat, 50 mL), and then extracted with EtOAc (80 mL×3). The organic layers were dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (PE/EtOAc (v/v)=2/1) to give the title compound as colorless oil (1.1 g, 71.9%).
Workup
- customThe reaction was quenched with NaHCO3 (sat, 50 mL)
- extractionextracted with EtOAc (80 mL×3)
- dry with materialThe organic layers were dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue was purified by silica gel column chromatography (PE/EtOAc (v/v)=2/1)
Sources & evidence
- ORD record
- ord-7db4584c6b79436a95b45fecb70dc303
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09394281B2
Reaction notes
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