Water → 4-(Nitromethyl)oxan-4-ol

HRID 44715

反応式

HRID 44715 の反応式
[O:1]1[CH2:6][CH2:5][C:4](=[O:7])[CH2:3][CH2:2]1.[N+:8]([CH3:11])([O-:10])=[O:9].[O-]CC.[Na+].O>C(O)C>[N+:8]([CH2:11][C:4]1([OH:7])[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1)([O-:10])=[O:9]

参加物

6

反応物 4

HCID 962WaterHCID 6375NitromethaneHCID 121599Tetrahydro-4H-pyran-4-oneHCID 2723922Sodium ethoxide

生成物 1

HCID 574578134-(Nitromethyl)oxan-4-ol収率 34%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

実験手順

A solution of tetrahydro-4H-pyran-4-one (45.0 g, 449 mmol) and nitromethane (36.5 mL, 674 mmol) in ethanol (27 mL) was treated with a solution of sodium ethoxide in ethanol (2.67 M, 8.40 mL, 22.5 mmol) using the method described in Part A of Example 9. The reaction mixture was transferred to a reparatory funnel and water (450 mL) was added. The mixture was extracted with ethyl acetate (3×900 mL). The organic layers were combined, dried over MgSO4, filtered, and concentrated to a light brown oil. Ethyl acetate/hexanes was added and pale brown crystals formed that were isolated by filtration and dried to provide 4-(nitromethyl)tetrahydro-2H-pyran-4-ol (24.4 g, 34%).

後処理

  1. customThe reaction mixture was transferred to a reparatory funnel
  2. extractionThe mixture was extracted with ethyl acetate (3×900 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to a light brown oil
  6. additionEthyl acetate/hexanes was added
  7. custompale brown crystals formed
  8. customthat were isolated by filtration
  9. customdried

出典と根拠

ORDレコード
ord-b1805ebd29684c9bab05620ab3dd9657
出典データセット
uspto-grants-2013_09
特許番号
US08541438B2

関連ノート

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