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

HRID 252764

反応式

HRID 252764 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-ac08051bbd874a95ae102b7fbb1a3e70
出典データセット
uspto-grants-2011_01
特許番号
US07868204B2

関連ノート

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