Tetrahydrofuran → HCID 18177295、化合物

HRID 610114ノート

反応式

HRID 610114 の反応式
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([CH:7]=[N:8][OH:9])=[CH:5][CH:4]=1.C[O:13][C:14](=[O:21])[C:15]([CH2:17][C:18]([OH:20])=[O:19])=[CH2:16].[CH2:22]1COCC1>>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]2[CH2:16][C:15]([C:14]([OH:13])=[O:21])([CH2:17][C:18]([O:20][CH3:22])=[O:19])[O:9][N:8]=2)=[CH:5][CH:4]=1

参加物

4

反応物 3

HCID 8028TetrahydrofuranHCID 94712N-[(4-Methoxyphenyl)methylidene]hydroxylamineHCID 4613903Butanedioic acid, 2-methylene-, methyl ester

生成物 1

HCID 18177295HCID 18177295、化合物収率 58%

実験手順

4-Methoxybenzaldehyde oxime (5.00 g, 33.1 mmol) and itaconic acid monomethyl ester (5.72 g, 39.7 mol) were added together with 200 mL of THF. To the above mixture was added bleach (84 mL of 0.67M aqueous solution) dropwise at room temperature. The reaction mixture was then stirred at RT under N2 for 12 h. The THF was removed in vacuo. The aqueous mixture was acidified with aqueous HCl and extracted with EtOAc. The EtOAc solution was washed with brine, dried over MgSO4, concentrated, and chromatographed with 10-30% MeOH in CH2Cl2 on silica gel to give 5.58 g of the desired product (58%). 1H NMR (DMSC-d6): δ63.08 (m, 2H); 3.61 (s, 3H); 3.55-3.87 (m, 2H); 3.80 (s, 3H); 7.00 (d, 2H); 7.61 (d, 2H).

後処理

  1. customThe THF was removed in vacuo
  2. extractionextracted with EtOAc
  3. washThe EtOAc solution was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customchromatographed with 10-30% MeOH in CH2Cl2 on silica gel

出典と根拠

ORDレコード
ord-234ec7f0e7d640d58fee777c3ec54bce
出典データセット
uspto-grants-1999_12
特許番号
US05998424

反応ノート

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