Tetrahydrofuran → 1-(2-(1,3-Dioxan-2-yl)ethylidene)-4-(3,4,5-trifluorophenyl)cyclohexane

HRID 975735ノート

反応式

HRID 975735 の反応式
[Br-].[O:2]1[CH2:7][CH2:6][CH2:5][O:4][CH:3]1[CH2:8][CH2:9][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1.CC(C)([O-])C.[K+].[F:40][C:41]1[CH:42]=[C:43]([CH:49]2[CH2:54][CH2:53][C:52](=O)[CH2:51][CH2:50]2)[CH:44]=[C:45]([F:48])[C:46]=1[F:47]>CCOCC>[O:4]1[CH2:5][CH2:6][CH2:7][O:2][CH:3]1[CH2:8][CH:9]=[C:52]1[CH2:51][CH2:50][CH:49]([C:43]2[CH:44]=[C:45]([F:48])[C:46]([F:47])=[C:41]([F:40])[CH:42]=2)[CH2:54][CH2:53]1

参加物

6

反応物 4

HCID 8028Tetrahydrofuran2 回HCID 27241682-(1,3-Dioxan-2-yl)ethyltriphenylphosphonium bromideHCID 219932844-(3,4,5-Trifluorophenyl)cyclohexan-1-oneHCID 23665647Potassium tert-butoxide

生成物 1

HCID 229157561-(2-(1,3-Dioxan-2-yl)ethylidene)-4-(3,4,5-trifluorophenyl)cyclohexane

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)ethyltriphenylphosphonium bromide (12.2 g, 27 mmols), followed by adding tetrahydrofuran (200 ml), suspending it, stirring under ice cooling till the liquid temperature reached 10° C., adding potassium t-butoxide (3.0 g, 27 mmols) to the reaction mixture, further elevating the temperature up to room temperature under ice cooling for one hour, stirring for one hour, dropwise adding a tetrahydrofuran (50 ml) solution of 4-(3,4,5-trifluorophenyl)cyclohexanone (5.7 g, 25 mmols) from the dropping funnel over 30 minutes, further stirring the reaction mixture for 5 hours after completion of the dropwise addition, adding ether (100 ml), allowing to stand for one hour, filtering off deposited insoluble substance, concentrating the filtrate under reduced pressure and isolating and purifying the resulting pale brown oil by means of silica gel column chromatography, to obtain 1-(2-(1,3-dioxan-2-yl)ethylidene)-4-(3,4,5-trifluorophenyl)cyclohexane.

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 oil by means of silica gel column chromatography

出典と根拠

ORDレコード
ord-381aea4bcde0463d856e93cb6f2eafcc
出典データセット
uspto-grants-1997_03
特許番号
US05609791

反応ノート

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