Tetrahydrofuran → 4-formyl-N-methoxymethyl-N-thiazol-2-yl-benzenesulfonamide

HRID 559506노트

반응식

HRID 559506 반응식
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]([CH2:18][O:19][CH3:20])[C:13]2[S:14][CH:15]=[CH:16][N:17]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1)#N.CC(C[AlH]CC(C)C)C.C1C[O:33]CC1>>[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]([CH2:18][O:19][CH3:20])[C:13]2[S:14][CH:15]=[CH:16][N:17]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1)=[O:33]

참가 물질

4

반응물 3

HCID 8028TetrahydrofuranHCID 14487Diisobutylaluminum hydrideHCID 670014474-cyano-N-methoxymethyl-N-thiazol-2-yl-benzenesulfonamide

생성물 1

HCID 866116984-formyl-N-methoxymethyl-N-thiazol-2-yl-benzenesulfonamide

실험 절차

To a solution of 4-cyano-N-methoxymethyl-N-thiazol-2-yl-benzenesulfonamide (4.5 mmol) in THF (50 mL) at −78° C. under argon was added DIBAL (5.0 mmol, 1M in THF) and the solution was allowed to warm to room temperature overnight. After the reaction was quenched with potassium sodium tartrate solution slowly, the mixture was extracted with ethyl acetate, and the organic phase was washed with brine, dried over MgSO4, and concentrated in vacuo. The crude product was purified by column chromatography to give 4-formyl-N-methoxymethyl-N-thiazol-2-yl-benzenesulfonamide (3.1 mmol).

후처리

  1. customAfter the reaction was quenched with potassium sodium tartrate solution slowly
  2. extractionthe mixture was extracted with ethyl acetate
  3. washthe organic phase was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by column chromatography

출처 및 근거

ORD 기록
ord-13bb3891a3c84102971122be65d9405f
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063080B2

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