6-(tetrahydro-2H-pyran-2-yloxy)hexahydrofuro[3,2-b]furan-3-ol → 6-((tetrahydro-2H-pyran-2-yl)oxy)tetrahydrofuro[3,2-b]furan-3(2H)-one

HRID 1053917노트

반응식

HRID 1053917 반응식
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH:8]1[CH:12]2[O:13][CH2:14][CH:15]([OH:16])[CH:11]2[O:10][CH2:9]1>C(Cl)Cl>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH:8]1[CH:12]2[O:13][CH2:14][C:15](=[O:16])[CH:11]2[O:10][CH2:9]1

참가 물질

3

반응물 1

HCID 767032036-(tetrahydro-2H-pyran-2-yloxy)hexahydrofuro[3,2-b]furan-3-ol

생성물 1

HCID 1183879426-((tetrahydro-2H-pyran-2-yl)oxy)tetrahydrofuro[3,2-b]furan-3(2H)-one수율 100.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
30 °C

실험 절차

To a solution of 6-((tetrahydro-2H-pyran-2-yl)oxy)hexahydrofuro[3,2-b]furan-3-ol (5.0 g, 21.7 mmol) in DCM (150 mL) was added DMP (18.4 g, 43.5 mmol) at rt, and then the mixture was stirred at 30° C. overnight and concentrated in vacuo. The residue was dissolved in water (150 mL), and extracted with EtOAc (150 mL×3). The combined organic phases were washed with brine (300 mL), dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (PE/EtOAc (v/v)=2/1) to give the title compound as yellow oil (4.96 g, 98%).

후처리

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in water (150 mL)
  3. extractionextracted with EtOAc (150 mL×3)
  4. washThe combined organic phases were washed with brine (300 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel column chromatography (PE/EtOAc (v/v)=2/1)

출처 및 근거

ORD 기록
ord-01fd0b8db1cd4816bb13ab0c8b6fca4d
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394281B2

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