Water → HCID 89963253、化合物

HRID 337880ノート

反応式

HRID 337880 の反応式
[H-].[Na+].[C@H:3]12[O:9][C@H:8]1[CH2:7][CH2:6][CH2:5][C@H:4]2[OH:10].[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[OH2:19]>C1COCC1>[CH2:11]([O:10][C@:4]1([OH:19])[CH2:5][CH2:6][CH2:7][C@H:8]2[C@H:3]1[O:9]2)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

参加物

6

反応物 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 330105AC1L766H

生成物 1

HCID 89963253HCID 89963253、化合物収率 51%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of sodium hydride (63%; 1.20 g, 31.5 mmol) in THF (20 mL), a solution of the (1R*,2R*,6S*)-7-oxabicyclo[4.1.0]heptan-2-ol (3.10 g, 27.2 mmol) prepared in Example 100a in THF (20 mL) was added with cooling on ice, and the mixture was stirred at room temperature for 1 hour. To the reaction solution, benzyl bromide (4.0 mL, 33.4 mmol) was added, and the mixture was stirred at room temperature for 12 hours. To the reaction solution, water (50 mL) was added, followed by extraction with ethyl acetate (50 mL). The thus obtained organic layer was dried over anhydrous sodium sulfate. After vacuum concentration, the residue was purified with silica gel chromatography (hexane/ethyl acetate=4:1) to yield the title compound (2.85 g, 51%) as a light brown oil.

後処理

  1. temperaturewith cooling on ice
  2. stirringthe mixture was stirred at room temperature for 12 hours
  3. extractionfollowed by extraction with ethyl acetate (50 mL)
  4. dry with materialThe thus obtained organic layer was dried over anhydrous sodium sulfate
  5. concentrationAfter vacuum concentration
  6. customthe residue was purified with silica gel chromatography (hexane/ethyl acetate=4:1)

出典と根拠

ORDレコード
ord-16e1b8293e0647809ce88222feb558d7
出典データセット
uspto-grants-2014_11
特許番号
US08889741B2

反応ノート

読み込み中…