Tetrabutylammonium Fluoride → 2-Chloro-N-(2-hydroxyethyl)-5-nitro-benzenesulfonamide

HRID 1259044ノート

反応式

HRID 1259044 の反応式
[Si]([O:18][CH2:19][CH2:20][NH:21][S:22]([C:25]1[CH:30]=[C:29]([N+:31]([O-:33])=[O:32])[CH:28]=[CH:27][C:26]=1[Cl:34])(=[O:24])=[O:23])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C.CCCCCC>O1CCCC1.C(OCC)(=O)C.[Cl-].[Na+].O>[Cl:34][C:26]1[CH:27]=[CH:28][C:29]([N+:31]([O-:33])=[O:32])=[CH:30][C:25]=1[S:22]([NH:21][CH2:20][CH2:19][OH:18])(=[O:24])=[O:23]

参加物

7

反応物 3

HCID 2724141Tetrabutylammonium FluorideHCID 21226206Ethyl acetate hexaneHCID 66690588n-[2-(Tert-butyldiphenylsilanyloxy)-ethyl]-2-chloro-5-nitro-benzenesulfonamide

生成物 1

HCID 145740892-Chloro-N-(2-hydroxyethyl)-5-nitro-benzenesulfonamide

試薬・触媒・溶媒 3

HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

The crude N-[2-(tert-butyldiphenylsilanyloxy)-ethyl]-2-chloro-5-nitro-benzenesulfonamide obtained above (theoretical 8.09 g) was dissolved in tetrahydrofuran (50 ml) and a 1M solution of tetrabutlyammonium fluoride in tetrahydrofuran (17.2 ml, 17.2 mmol) was added in one portion. The reaction was stirred at room temperature for 2 h then diluted with ethyl acetate (30 ml) and brine (30 ml), the organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The reaction was purified by column chromatography using hexane: ethyl acetate as eluent to afford the named product (3.44 g, 79% over 2 steps); Rf (ethyl acetate:hexane 1:1) 0.11, LCMS Rt=2.85 min, m/z (ES−) 279 (M−H).

後処理

  1. dry with materialthe organic layer was dried over sodium sulfate
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customThe reaction was purified by column chromatography
  5. customethyl acetate as eluent to afford the named product (3.44 g, 79% over 2 steps)

出典と根拠

ORDレコード
ord-0d762b250d2943879dccfb677f792a28
出典データセット
uspto-grants-2013_06
特許番号
US08466201B2

反応ノート

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