6-Methoxy-2-phenyl-5-hydroxymethylbenzothiazole → 6-Methoxy-2-phenyl-benzothiazol-5-aldehyde

HRID 1459599ノート

反応式

HRID 1459599 の反応式
[CH3:1][O:2][C:3]1[C:17]([CH2:18][OH:19])=[CH:16][C:6]2[N:7]=[C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[S:9][C:5]=2[CH:4]=1>CC(CC(C)C)=O.[O-2].[O-2].[Mn+4]>[CH3:1][O:2][C:3]1[C:17]([CH:18]=[O:19])=[CH:16][C:6]2[N:7]=[C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[S:9][C:5]=2[CH:4]=1

参加物

4

反応物 1

HCID 226200816-Methoxy-2-phenyl-5-hydroxymethylbenzothiazole

生成物 1

HCID 226200646-Methoxy-2-phenyl-benzothiazol-5-aldehyde収率 22.3%

試薬・触媒・溶媒 2

HCID 178418406HCID 178418406、化合物触媒HCID 7909Methyl Isobutyl Ketone溶媒

実験手順

A solution of 10.94 grams (40.4 mmol) 6-methoxy-2-phenyl-5-hydroxymethylbenzothiazole (as part of a mixture of regioisomeric alcohols) in 600 mL of methylisobutyl ketone was treated with 42 grams (484 mmol) of manganese dioxide. The mixture was heated under reflux for 1.5 hours and was then filtered through Celite®. The filtrate was evaporated in vacuo and the residue was chromatographed on silica (elution with 9/1 hexane/ethyl acetate). Mixed fractions were rechromatographed on silica using 95/5 hexane/ethyl acetate to afford a total of 2.43 grams of the desired aldehyde.

後処理

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 1.5 hours
  3. filtrationwas then filtered through Celite®
  4. customThe filtrate was evaporated in vacuo
  5. customthe residue was chromatographed on silica (elution with 9/1 hexane/ethyl acetate)
  6. customMixed fractions were rechromatographed on silica using 95/5 hexane/ethyl acetate

出典と根拠

ORDレコード
ord-c86ec66dae2d48d7b0ac3e2d0a2754cf
出典データセット
uspto-grants-1998_12
特許番号
US05854262

反応ノート

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