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

HRID 1259044노트

반응식

HRID 1259044 반응식
[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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매HCID 57417360Sodium chloride; water용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-0d762b250d2943879dccfb677f792a28
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08466201B2

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