m-Chloroperbenzoic acid → 1,5:2,3-Dianhydro-3-C-(3-bromophenyl)-4-deoxypentitol

HRID 1693238노트

반응식

HRID 1693238 반응식
ClC1C=CC=C(C(OO)=[O:9])C=1.[Br:12][C:13]1[CH:14]=[C:15]([C:19]2[CH2:20][CH2:21][O:22][CH2:23][CH:24]=2)[CH:16]=[CH:17][CH:18]=1.C(=O)(O)[O-].[Na+]>ClCCl>[Br:12][C:13]1[CH:14]=[C:15]([C:19]23[O:9][CH:20]2[CH2:21][O:22][CH2:23][CH2:24]3)[CH:16]=[CH:17][CH:18]=1

참가 물질

5

반응물 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 57475766HCID 57475766, 화합물

생성물 1

HCID 578277501,5:2,3-Dianhydro-3-C-(3-bromophenyl)-4-deoxypentitol수율 76.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

3-Chloroperbenzoic acid (purity: 80%, 25.1 g) was added to a solution of 4-(3-bromophenyl)-3,6-dihydro-2H-pyran (21.4 g) in dichloromethane (400 mL) in an ice bath. The mixture was stirred at the same temperature for three hours, and then warmed to room temperature and stirred for five hours. Ice and a saturated sodium bicarbonate solution were added to the reaction mixture, and the organic layer was separated. The organic layer was sequentially washed with a saturated sodium bicarbonate solution, a sodium thiosulfate solution and brine. The aqueous layers were combined and extracted with ethyl acetate, and the organic layer was sequentially washed with a sodium bicarbonate solution, a sodium thiosulfate solution and brine. The organic layers were combined and 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 (17.5 g).

후처리

  1. stirringstirred for five hours
  2. customthe organic layer was separated
  3. washThe organic layer was sequentially washed with a saturated sodium bicarbonate solution
  4. extractionextracted with ethyl acetate
  5. washthe organic layer was sequentially washed with a sodium bicarbonate solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-5c4d31ee281d42bb97774a7de0caf0c9
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08158620B2

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