Tetrahydrofuran → 4-(4-Propylcyclohexyl)cyclohexane

HRID 975742

反応式

HRID 975742 の反応式
[Br-].C1([PH+](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O1CCCC1.CC(C)([O-])C.[K+].[CH2:32]([CH:35]1[CH2:40][CH2:39][CH:38]([CH:41]2[CH2:46][CH2:45][C:44](=O)[CH2:43][CH2:42]2)[CH2:37][CH2:36]1)[CH2:33][CH3:34]>CCOCC>[CH2:32]([CH:35]1[CH2:40][CH2:39][CH:38]([CH:41]2[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]2)[CH2:37][CH2:36]1)[CH2:33][CH3:34]

参加物

6

反応物 4

HCID 8028Tetrahydrofuran2 回HCID 517696Phosphine, triphenyl-, hydrobromideHCID 4354185[1,1'-Bicyclohexyl]-4-one,4'-propyl-,HCID 23665647Potassium tert-butoxide

生成物 1

HCID 178840974-(4-Propylcyclohexyl)cyclohexane収率 56%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

Into a three-necked flask equipped with a dropping funnel, a three-way cock and a thermometer was placed (2-(1,3-dioxan)-2-yl)ethyl)triphenylphosphonium bromide (12.3 g, 27 mmols), followed by adding tetrahydrofuran (50 ml), suspending, stirring under ice cooling till the liquid temperature reached 10° C. The reaction mixture is added potassium t-butoxide (3.0 g, 27 mmols), followed by elevating the temperature up to room temperature under ice cooling for one hour, stirring for one hour, dropwise adding a tetrahydrofuran (10 ml) solution of 4-(4-propylcyclohexyl)cyclohexanone (15.6 g, 25 mmols) over 30 minutes from the dropping funnel, further stirring the reaction mixture for 5 hours after completion of the dropwise addition, adding ether (50 ml), allowing to stand for one hour, filtering off deposited insoluble substance, concentrating the filtrate under reduced pressure, isolating and purifying the resulting pale brown oily substance by means of silica gel column chromatography and recrystallizing from ethanol, to obtain 1-(2-(1,3-dioxan)-2-yl)ethylidene)-4-(4-propylcyclohexyl)cyclohexane (4.5 g, 14 mmols).

後処理

  1. customInto a three-necked flask equipped with a dropping funnel
  2. customreached 10° C
  3. customup to room temperature
  4. customfor one hour
  5. stirringstirring for one hour
  6. stirringfurther stirring the reaction mixture for 5 hours
  7. additionafter completion of the dropwise addition
  8. filtrationfiltering off
  9. concentrationconcentrating the filtrate under reduced pressure
  10. customisolating
  11. custompurifying the resulting pale brown oily substance by means of silica gel column chromatography
  12. customrecrystallizing from ethanol

出典と根拠

ORDレコード
ord-b6001f375b1c4dde9bc2c80ccc1b1963
出典データセット
uspto-grants-1997_03
特許番号
US05609791

関連ノート

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