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Ethanol → (4-(3-Propylcyclopentyl)cyclohexyl)methanol

HRID 2358889
ノート
印刷プレビュー

反応式

HRID 2358889 の反応式
C(O)C.[CH2:4]([CH:7]1[CH2:11][CH2:10][CH:9]([CH:12]2[CH2:17][CH2:16][CH:15]([CH:18]=[O:19])[CH2:14][CH2:13]2)[CH2:8]1)[CH2:5][CH3:6].[BH4-].[Na+]>O>[CH2:4]([CH:7]1[CH2:11][CH2:10][CH:9]([CH:12]2[CH2:17][CH2:16][CH:15]([CH2:18][OH:19])[CH2:14][CH2:13]2)[CH2:8]1)[CH2:5][CH3:6]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 866602914-(3-Propylcyclopentyl)cyclohexanecarboaldehyde

生成物 1

HCID 67992361(4-(3-Propylcyclopentyl)cyclohexyl)methanol収率 90.5%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

Ethanol (30 ml) was added to 4-(3-propylcyclopentyl)cyclohexanecarboaldehyde (2.3 g) obtained in the second step in Example 3, in a reaction vessel under an atmosphere of nitrogen, and the mixture was cooled to 0° C., and sodium borohydride (0.22 g) was added slowly. After the mixture had been returned to room temperature and stirred for another 20 hours and water (30 ml) was added. The mixture was separated, and the water layer was extracted with diethyl ether three times, and then the combined organic layer was washed with brine. The solution was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (eluent: ethyl acetate/n-heptane=½ by volume) to give (4-(3-propylcyclopentyl)cyclohexyl)methanol (2.1 g).

後処理

  1. customobtained in the second step in Example 3, in a reaction vessel under an atmosphere of nitrogen
  2. customhad been returned to room temperature
  3. customThe mixture was separated
  4. extractionthe water layer was extracted with diethyl ether three times
  5. washthe combined organic layer was washed with brine
  6. dry with materialThe solution was dried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified by silica gel chromatography (eluent: ethyl acetate/n-heptane=½ by volume)

出典と根拠

ORDレコード
ord-a53682817a5d4772b33647ce6ac8464c
出典データセット
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08685274B2

反応ノート

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