Triethylamine → 6-(2-(Benzyloxy)ethoxy)hexahydrofuro[3,2-b]furan-3-yl methanesulfonate
Reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][O:11][CH:12]1[CH:16]2[O:17][CH2:18][CH:19]([OH:20])[CH:15]2[O:14][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:28][S:29]([O:20][CH:19]1[CH2:18][O:17][CH:16]2[CH:12]([O:11][CH2:10][CH2:9][O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:13][O:14][CH:15]12)(=[O:31])=[O:30]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a suspension of 6-(2-(benzyloxy)ethoxy)hexahydrofuro[3,2-b]furan-3-ol (1.50 g, 5.36 mmol) in anhydrous DCM (20 mL) was added N,N-diethylethanamine (1.20 mL, 8.60 mmol) and N,N-dimethylpyridin-4-amine (0.13 g, 1.07 mmol) under the nitrogen atmosphere, and the mixture was cooled down to 0° C. To the mixture was added methanesulfonyl chloride (0.50 mL, 6.50 mmol) at 0° C., and then the mixture was moved to room temperature and stirred overnight. The mixture was diluted with DCM (50 mL), washed with brine (50 mL) and dried over anhydrous Na2SO4, then filtered and concentrated in vacuo. The residue was purified by silica chromatography (EtOAc/PE (v/v)=2/1) to give the title compound as yellow liquid (1.81 g, 94%).
Workup
- customwas moved to room temperature
- washwashed with brine (50 mL)
- dry with materialdried over anhydrous Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue was purified by silica chromatography (EtOAc/PE (v/v)=2/1)
Sources & evidence
- ORD record
- ord-dce2d97087ad475e8191dbc673fc1d92
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09394281B2
Reaction notes
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