反応 #740641

反応方程式

5,6-dihydro-4H-thieno[2,3-b]thiopyran-4-one-2-sulfonamide

water

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material

収率 80.0%

5,6-Dihydro-5-bromo-4H-thieno[2,3-b]thiopyran-4-one-2-sulfonamide

収率 80.0%

溶媒

tetrahydrofuran

tetrahydrofuran

acetonitrile

反応条件

後処理

1. 1
   workup.ADDITIONwas added over 15 minutes
2. 2
   濃縮concentrated in vacuo
3. 3
   その他to remove tetrahydrofuran and acetonitrile
4. 4
   抽出The aqueous mixture was extracted with ethyl acetate (3×100 ml)
5. 5
   洗浄the combined extracts were washed with water
6. 6
   乾燥dried over sodium sulfate
7. 7
   濃縮concentrated to dryness in vacuo
8. 8
   その他The residue was partially purified by chromatography on silica gel
9. 9
   洗浄eluting with 50% ethyl acetate-hexane

実験手順

A solution of 5,6-dihydro-4H-thieno[2,3-b]thiopyran-4-one-2-sulfonamide (3.50 g, 0.014 m) in dry tetrahydrofuran (70 ml) was stirred at ambient temperature while a solution of pyridinium bromide perbromide (6.08 g, 0.019 m) in dry tetrahydrofuran (35 ml) and acetonitrile (10 ml) was added over 15 minutes. After stirring at ambient temperature for 1 hour, the reaction mixture was added to water (100 ml) and concentrated in vacuo to remove tetrahydrofuran and acetonitrile. The aqueous mixture was extracted with ethyl acetate (3×100 ml), the combined extracts were washed with water, dried over sodium sulfate and concentrated to dryness in vacuo. The residue was partially purified by chromatography on silica gel, eluting with 50% ethyl acetate-hexane, to yield 3.68 g (80%) of material which was used in the next reaction without further purification.

出典