反応式
[CH3:1][C:2]1([CH3:14])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:13]=[CH:12][O:11][CH:10]=2)[O:3]1.ClS([N:19]=[C:20]=[O:21])(=O)=O.O1C=CC=C1>C(#N)C.O.C(Cl)Cl>[CH3:8][C:6]1([CH3:7])[C:2]([CH3:14])([CH3:1])[O:3][B:4]([C:9]2[CH:13]=[C:12]([C:20]([NH2:19])=[O:21])[O:11][CH:10]=2)[O:5]1参加物
実験手順
3-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-furan (5.0 g, 25.77 mmol) is dissolved in dry acetonitrile (30 mL). Chlorosulfonylisocyanate (5.47 g, 38.65 mmol, 1.5 equiv.) in solution in dry acetonitrile (20 mL) is added in one portion at room temperature to the furan producing a pink solution that subsides overnight to turn yellow. The resulting solution is cooled with an ice bath and water (5 mL) is added, causing an exotherm. The resulting mixture is partitionned between DCM (100 mL) and water (30 mL). The aqueous layer is extracted 3 more times with DCM (50 mL), then the organic layers are gathered, washed with brine (10 mL), dried over anhydrous Na2SO4 and finally the solvent is removed under vacuum. The oily residue is dissolved in DCM (3 mL), sonicated to give a suspension of a crystalline solid. The solid is separated by filtration, and the cake is washed with a very small amount of DCM, then diethyl ether and dried under suction to afford 3 g of the title compound as a white powder.
後処理
- temperatureThe resulting solution is cooled with an ice bath
- extractionThe aqueous layer is extracted 3 more times with DCM (50 mL)
- washwashed with brine (10 mL)
- dry with materialdried over anhydrous Na2SO4
- customfinally the solvent is removed under vacuum
- dissolutionThe oily residue is dissolved in DCM (3 mL)
- customsonicated
- customto give
- additiona suspension of a crystalline solid
- customThe solid is separated by filtration
- washthe cake is washed with a very small amount of DCM
- dry with materialdiethyl ether and dried under suction
出典と根拠
- ORDレコード
- ord-c973243a454c47948075c5d0123bb4ce
- 出典データセット
- uspto-grants-2011_09
- 特許番号
- US08012983B2
関連ノート
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