Water → [1,2,5]Thiadiazolo[3,4-b]pyridine-6-carbaldehyde

HRID 1943232노트

반응식

HRID 1943232 반응식
C1(/C=[CH:8]/[C:9]2[CH:14]=[N:13][C:12]3=[N:15][S:16][N:17]=[C:11]3[CH:10]=2)C=CC=CC=1.C[N+]1([O-])CC[O:22]CC1.O.I([O-])(=O)(=O)=O.[Na+]>[Os](=O)(=O)(=O)=O.O.CC(C)=O>[N:17]1[S:16][N:15]=[C:12]2[C:11]=1[CH:10]=[C:9]([CH:8]=[O:22])[CH:14]=[N:13]2

참가 물질

8

반응물 4

HCID 962WaterHCID 82029Methyl morpholine oxideHCID 23667635Sodium periodateHCID 685963166-[(E)-2-Phenylethenyl][1,2,5]thiadiazolo[3,4-b]pyridine

생성물 1

HCID 82414701[1,2,5]Thiadiazolo[3,4-b]pyridine-6-carbaldehyde

시약·촉매·용매 3

HCID 962Water촉매HCID 30318Osmium Tetroxide촉매HCID 180Acetone용매

실험 절차

To 6-[(E)-2-phenylethenyl][1,2,5]thiadiazolo[3,4-b]pyridine (0.88 g, 3.68 mmol) was added acetone (30 ml), N-methyl-morpholine-N-oxide, 50 wt. % in water (1.525 ml, 7.35 mmol) and then osmium tetroxide in water (0.225 ml, 0.037 mmol). The reaction was then stirred for 20 hours. To the pale brown solution was added sodium periodate (3.15 g, 14.71 mmol) and stirring continued for 45 mins. The solvent was reduced by rotary evaporation and the remainder partitioned between chloroform and water. The aqueous was further extracted with chloroform and the combined organic extracts passed through a hydrophobic frit and concentrated to give brown/black solid (0.6 g). A portion of this material (0.575 g) was purified by chromatography on silica eluting with 20% EtOAc in cyclohexane to a pale yellow solid (160 mg).

후처리

  1. stirringstirring
  2. waitcontinued for 45 mins
  3. customThe solvent was reduced by rotary evaporation
  4. customthe remainder partitioned between chloroform and water
  5. extractionThe aqueous was further extracted with chloroform
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-c6af9bcf5f2141ba9d52ca1a3bb07de5
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08389524B2

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