Benzenesulfonyl hydrazide → Methyl 4-(4-oxo-chroman-3-ylmethyl)-benzoate

HRID 252764

반응식

HRID 252764 반응식
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][CH2:4][C:3]1=[CH:12][C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=1.C1(S(NN)(=O)=O)C=CC=CC=1>CN(C=O)C>[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][CH2:4][CH:3]1[CH2:12][C:13]1[CH:14]=[CH:15][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:21][CH:22]=1

참가 물질

4

반응물 2

HCID 65723Benzenesulfonyl hydrazideHCID 4240115Methyl 4-(4-oxo-chroman-3-ylidenemethyl)-benzoate

생성물 1

HCID 22478914Methyl 4-(4-oxo-chroman-3-ylmethyl)-benzoate수율 42.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

A suspension of 260 (400 mg, 1.36 mmol) and benzenesulfonyl hydrazine (702 mg, 4.08 mmol) in DMF (7 ml) was stirred at 100° C. during 48 h. The solvent was evaporated and the residue was diluted in AcOEt, washed with NH4Cl sat., brine, dried over anhydrous MgSO4, filtered and concentrated. The crude residue was then purified by flash chromatography on silica gel (5% AcOEt/HEx) to afford the title compound 264 (170 mg, 42%) as a white solid. LRMS: 296.1 (Calc.); 297.0 (found).

후처리

  1. customThe solvent was evaporated
  2. additionthe residue was diluted in AcOEt
  3. washwashed with NH4Cl sat., brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude residue was then purified by flash chromatography on silica gel (5% AcOEt/HEx)

출처 및 근거

ORD 기록
ord-ac08051bbd874a95ae102b7fbb1a3e70
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07868204B2

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