Pyridine → 6-Hydroxyhexahydrofuro[3,2-b]furan-3-yl 4-methylbenzenesulfonate
Reaction equation
[O:1]1[CH2:5][CH:4]([OH:6])[CH:3]2[O:7][CH2:8][CH:9]([OH:10])[CH:2]12.N1C=CC=CC=1.[CH3:17][C:18]1[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1>ClCCl>[CH3:17][C:18]1[CH:23]=[CH:22][C:21]([S:24]([O:6][CH:4]2[CH2:5][O:1][CH:2]3[CH:9]([OH:10])[CH2:8][O:7][CH:3]23)(=[O:26])=[O:25])=[CH:20][CH:19]=1Participants
5
Conditions
- Temperature
- 0 °C
Procedure
To a solution of hexahydrofuro[3,2-b]furan-3,6-diol (10.00 g, 68.4 mmol) in dichloromethane (60 mL) was added pyridine (1.08 g, 13.7 mmol) and then the mixture was cooled to 0° C., and 4-methylbenzenesulfonyl chloride (15.66 g, 82.1 mmol) was added. The mixture was stirred at 0° C. for 30 min, and then warmed to room temperature overnight. The resulting mixture was diluted with dichloromethane (250 mL), washed with 1M HCl (300 mL) followed by water (300 mL) and brine (300 mL). The separated organic phase was dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified with a silica gel column chromatography (EtOAc/PE (v/v)=2/1) to afford the desired product as colorless oil (10.24 g, 49.8%).
Workup
- temperaturewarmed to room temperature overnight
- washwashed with 1M HCl (300 mL)
- dry with materialThe separated organic phase was dried over anhydrous Na2SO4
- concentrationconcentrated in vacuo
- customThe residue was purified with a silica gel column chromatography (EtOAc/PE (v/v)=2/1)
Sources & evidence
- ORD record
- ord-71d2b0567e16471799adde35b2deef8e
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09394281B2
Reaction notes
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