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

HRID 975735노트

반응식

HRID 975735 반응식
[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

참가 물질

6

반응물 4

HCID 8028Tetrahydrofuran2회HCID 27241682-(1,3-Dioxan-2-yl)ethyltriphenylphosphonium bromideHCID 219932844-(3,4,5-Trifluorophenyl)cyclohexan-1-oneHCID 23665647Potassium tert-butoxide

생성물 1

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

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-381aea4bcde0463d856e93cb6f2eafcc
출처 데이터셋
uspto-grants-1997_03
특허 번호
US05609791

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