Sodium Hypochlorite → (3AR,5R)-5-((benzyloxy)methyl)-3a,4,5,7-tetrahydro-3H-pyrano[3,4-c]isoxazole

HRID 217987

반응식

HRID 217987 반응식
[CH2:1]([O:8][CH2:9][C@H:10]([O:14][CH2:15][CH:16]=[N:17][OH:18])[CH2:11][CH:12]=[CH2:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[O-].[Na+]>ClCCl.O>[CH2:1]([O:8][CH2:9][C@@H:10]1[O:14][CH2:15][C:16]2=[N:17][O:18][CH2:13][C@@H:12]2[CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 2

HCID 23665760Sodium HypochloriteHCID 86640913((R)-1-benzyloxymethyl-3-butenyloxy)acetaldehyde oxime

생성물 1

HCID 57475687(3AR,5R)-5-((benzyloxy)methyl)-3a,4,5,7-tetrahydro-3H-pyrano[3,4-c]isoxazole수율 89.8%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

((R)-1-Benzyloxymethyl-3-butenyloxy)acetaldehyde oxime (13.7 g) was dissolved in dichloromethane (164 ml). A 5% sodium hypochlorite solution (164 ml) was added dropwise in an ice bath, and the mixture was stirred at the same temperature for two hours. The reaction solution was diluted with water, and the aqueous layer was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (12.2 g).

후처리

  1. extractionthe aqueous layer was extracted with dichloromethane
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-3d71e4cd012844d2b3d99c2cdf9c16d4
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08198269B2

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