Hydrogen Peroxide → (2RS,3SR,5E)-3-(4-chlorophenyl)-6-(2-naphthyl)-5-hexen-2-ol

HRID 263677ノート

反応式

HRID 263677 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:12]/[CH:13]=[CH:14]/[C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=2)[C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1.C([BH-](C(CC)C)C(CC)C)(CC)C.[Li+].[OH-].[Na+].OO>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:12]/[CH:13]=[CH:14]/[C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=2)[CH:9]([OH:11])[CH3:10])=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 3611392Lithium tri-s-butylborohydrideHCID 19038600(E)-3-(4-chlorophenyl)-6-(2-naphthyl)-5-hexen-2-one

生成物 1

HCID 19038652(2RS,3SR,5E)-3-(4-chlorophenyl)-6-(2-naphthyl)-5-hexen-2-ol収率 84.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

4.78 g of (E)-3-(4-chlorophenyl)-6-(2-naphthyl)-5-hexen-2-one was dissolved in 30 ml of tetrahydrofuran, and 14.3 ml of a 1M tetrahydrofuran solution of lithium tri-sec-butyl borohydride was added at -78° C. under cooling with stirring, followed by stirring at the same temperature for 2 hours. To the reaction solution, 10 ml of a 2N sodium hydroxide aqueous solution was added under cooling with ice with stirring, and then, 15 ml of a 30% hydrogen peroxide aqueous solution was gradually dropwise added, followed by stirring at room temperature for one hour. The reaction solution was extracted by an addition of ethyl ether and water. The organic layer was washed with a saturated sodium thiosulfate aqueous solution and a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The drying agent was filtered off, and then, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=15/1→5/1) to obtain 4.06 g of the above-identified compound.

後処理

  1. temperatureunder cooling
  2. stirringby stirring at the same temperature for 2 hours
  3. temperatureunder cooling with ice
  4. stirringwith stirring
  5. stirringby stirring at room temperature for one hour
  6. extractionThe reaction solution was extracted by an addition of ethyl ether and water
  7. washThe organic layer was washed with a saturated sodium thiosulfate aqueous solution
  8. dry with materiala saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate
  9. filtrationThe drying agent was filtered off
  10. distillationthe solvent was distilled off under reduced pressure
  11. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=15/1→5/1)

出典と根拠

ORDレコード
ord-43f15f69195e48ddb29fa27313480df1
出典データセット
uspto-grants-1997_07
特許番号
US05643958

反応ノート

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