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

HRID 840608

반응식

HRID 840608 반응식
[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

참가 물질

4

반응물 1

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

생성물 1

HCID 226200646-Methoxy-2-phenyl-benzothiazol-5-aldehyde수율 22.3%

시약·촉매·용매 2

HCID 178418406HCID 178418406, 화합물촉매HCID 7909Methyl Isobutyl Ketone용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-37a4fd4138f14250a2ae58cd7a207620
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06369074B1

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