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

HRID 217987

反応式

HRID 217987 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

((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).

後処理

  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

出典と根拠

ORDレコード
ord-3d71e4cd012844d2b3d99c2cdf9c16d4
出典データセット
uspto-grants-2012_06
特許番号
US08198269B2

関連ノート

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