Pyridine → 7-furyl-3-methyl-4-chromanone O-(toluenesulfonyl)-oxime

HRID 1059670ノート

反応式

HRID 1059670 の反応式
[C:1]1([CH3:11])[C:2]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.[O:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[C:17]1[CH:26]=[C:25]2[C:20]([C:21](=[N:28][OH:29])[CH:22]([CH3:27])[CH2:23][O:24]2)=[CH:19][CH:18]=1.N1C=CC=CC=1>C(Cl)Cl>[C:1]1([CH3:11])[C:2]([S:7]([O:29][N:28]=[C:21]2[C:20]3[C:25](=[CH:26][C:17]([C:13]4[O:12][CH:16]=[CH:15][CH:14]=4)=[CH:18][CH:19]=3)[O:24][CH2:23][CH:22]2[CH3:27])(=[O:9])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

5

反応物 3

HCID 1049PyridineHCID 8623o-Toluenesulfonyl chlorideHCID 73868111HCID 73868111、化合物

生成物 1

HCID 865864777-furyl-3-methyl-4-chromanone O-(toluenesulfonyl)-oxime収率 57.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

Toluenesulfonyl chloride (397 mg, 2.08 mmol) was added to a 0° C. solution of 7-furyl-3-methyl-4-chromanone oxime (61) (461 mg, 1.89 mmol) and pyridine (0.5 mL) in CH2Cl2 (10 mL). After 6 hours, the mixture was diluted with CH2Cl2 (30 mL) and washed with 59 HCl (20 mL). The organic layer was dried over MgSO4, filtered and concentrated. The residue was purified via flash chromatography using 5:1 hexanes:EtOAc as the eluent, to provide 7-furyl-3-methyl-4-chromanone O-(toluenesulfonyl)-oxime (62) (429 mg) as a pink solid, m.p. 163-164° C. (dec).

後処理

  1. washwashed with 59 HCl (20 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified via flash chromatography

出典と根拠

ORDレコード
ord-74bc0f9d401c43f09f1c547d4dd0a731
出典データセット
uspto-grants-2003_02
特許番号
US06521622B1

反応ノート

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