3,4-dihydro-2H-pyran → 6-(tetrahydro-2H-pyran-2-yloxy)hexahydrofuro[3,2-b]furan-3-ol

HRID 1053916ノート

反応式

HRID 1053916 の反応式
[O:1]1[CH2:5][CH:4]([OH:6])[CH:3]2[O:7][CH2:8][CH:9]([OH:10])[CH:2]12.[CH2:11]1[CH2:16][O:15][CH:14]=[CH:13][CH2:12]1>C(Cl)Cl>[O:15]1[CH2:16][CH2:11][CH2:12][CH2:13][CH:14]1[O:6][CH:4]1[CH:3]2[O:7][CH2:8][CH:9]([OH:10])[CH:2]2[O:1][CH2:5]1

参加物

4

反応物 2

HCID 80803,4-dihydro-2H-pyranHCID 999371,4:3,6-Dianhydromannitol

生成物 1

HCID 767032036-(tetrahydro-2H-pyran-2-yloxy)hexahydrofuro[3,2-b]furan-3-ol収率 45%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of hexahydrofuro[3,2-b]furan-3,6-diol (10.0 g, 68.50 mmol) in DCM (150 mL) was added PPTs (1.7 g, 6.85 mmol) at rt followed by DHP (6.0 g, 71.90 mmol) slowly in 2 h, and then the mixture was stirred at rt 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), then dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (PE/EtOAc (v/v)=1/1) to give the title compound as a white solid (7.1 g, 45%).

後処理

  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)=1/1)

出典と根拠

ORDレコード
ord-7d662ef3abdb445ea8536911dd8c7444
出典データセット
uspto-grants-2016_07
特許番号
US09394281B2

反応ノート

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