Tetrahydrofuran → HCID 66834488, compound
Reaction equation
C1COCC1.[CH3:6][O:7][C:8]1[C:9]([S:21](Cl)(=[O:23])=[O:22])=[CH:10][C:11]2[CH2:12][CH2:13][C:14](=[O:20])[C:15]([CH3:19])([CH3:18])[C:16]=2[CH:17]=1.[NH:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1.C(N(CC)CC)C>O>[CH3:6][O:7][C:8]1[CH:17]=[C:16]2[C:11]([CH2:12][CH2:13][C:14](=[O:20])[C:15]2([CH3:19])[CH3:18])=[CH:10][C:9]=1[S:21]([N:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1)(=[O:23])=[O:22]Participants
Conditions
- Temperature
- 0 °C
Procedure
The THF (4 ml) solution of 3-methoxy-5,5-dimethyl-6-oxo-5,6,7,8-tetrahydro-naphthalen-2-sulfonyl chloride (Compound CC1, 295 mg, 0.974 mmol) was cooled to 0° C., and the tetrafuran (1 ml) solution combining pyrrolidine (121 μl, 1.5 eq.) and triethylamine (272 μl, 2 eq.) was added dropwise thereto over 2 min. The mixture was stirred at 0° C. until Compound CC-1 disappears. The reaction solution was added with distilled water and extracted with ethyl acetate. The organic layer was washed with 10% aqueous solution of disodium ethylenediamine tetraacetic acid. The organic layer was washed with brine and dried over sodium sulfate. The drying agent was removed by filtration and the residues obtained after concentration under reduced pressure were purified by silica gel column chromatography (ethyl acetate/hexane) to obtain the title compound (246 mg, 75%).
Workup
- additionwas added dropwise
- extractionextracted with ethyl acetate
- washThe organic layer was washed with 10% aqueous solution of disodium ethylenediamine tetraacetic acid
- washThe organic layer was washed with brine
- dry with materialdried over sodium sulfate
- customThe drying agent was removed by filtration
- customthe residues obtained
- concentrationafter concentration under reduced pressure
- customwere purified by silica gel column chromatography (ethyl acetate/hexane)
Sources & evidence
- ORD record
- ord-7fbf964429d643278ede688c30d7e3e5
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09440922B2
Reaction notes
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