Diethyl Ether → 1-(4-fluorophenyl)-4-(4-(4-pentylcyclohexyl)cyclohexyl)-2Z-butene

HRID 1609433ノート

反応式

HRID 1609433 の反応式
[Br-].[F:2][C:3]1[CH:29]=[CH:28][C:6]([CH2:7][CH2:8][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:5][CH:4]=1.CC(C)([O-])C.[K+].[CH2:36]([CH:41]1[CH2:46][CH2:45][CH:44]([CH:47]2[CH2:52][CH2:51][CH:50]([CH2:53][CH:54]=O)[CH2:49][CH2:48]2)[CH2:43][CH2:42]1)[CH2:37][CH2:38][CH2:39][CH3:40].CCOCC>C1COCC1>[F:2][C:3]1[CH:4]=[CH:5][C:6](/[CH:7]=[CH:8]\[CH2:54][CH2:53][CH:50]2[CH2:51][CH2:52][CH:47]([CH:44]3[CH2:43][CH2:42][CH:41]([CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH2:46][CH2:45]3)[CH2:48][CH2:49]2)=[CH:28][CH:29]=1

参加物

6

反応物 4

HCID 3283Diethyl EtherHCID 111404394-(4-Pentylcyclohexyl)cyclohexylacetoaldehydeHCID 223867454-Fluorophenethyltriphenylphosphonium bromideHCID 23665647Potassium tert-butoxide

生成物 1

HCID 867485941-(4-fluorophenyl)-4-(4-(4-pentylcyclohexyl)cyclohexyl)-2Z-butene収率 57.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

4-fluorophenethyltriphenylphosphoniumbromide (4.2 g, 9 mmol) was dried and then dissolved in THF (10 ml), followed by stirring under ice cooling, adding potassium-t-butoxide (1.0 g, 9 mmol) slowly to the obtained reaction solution, stirring at room temperature for 2 hours after the completion of dropping, adding a THF (50 ml) solution of 4-(4-pentylcyclohexyl)-cyclohexylacetoaldehyde (2.7 g, 9.7 mmol) and further stirring for 5 hours, adding ether after the completion of reaction, filtering off the obtained white crystals deposited, concentrating the filtrate under reduced pressure, and purifying the obtained brown oil by means of silica gel column chromatography, to obtain a mixture (2.0 g, 5.2 mmol) of 1-(4-fluorophenyl)-4-(4-(4-pentylcyclohexyl)cyclohexyl)-2Z-butene with its E-isomer.

後処理

  1. customslowly to the obtained reaction solution
  2. stirringstirring at room temperature for 2 hours after the completion
  3. stirringfurther stirring for 5 hours
  4. customafter the completion of reaction
  5. filtrationfiltering off the obtained white crystals
  6. concentrationconcentrating the filtrate under reduced pressure
  7. custompurifying the obtained brown oil by means of silica gel column chromatography

出典と根拠

ORDレコード
ord-f620ef707b3340d28e49755e170121b4
出典データセット
uspto-grants-1995_03
特許番号
US05401434

反応ノート

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