Diethyl Ether → 2-Allyl-6-[(butylthio)methylene]-2-ethylcyclohexanone

HRID 65615노트

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HRID 65615 반응식
[CH3:1][C:2](C)([O-])C.[K+].[CH2:7]([S:11][CH:12]=[C:13]1[CH2:18][CH2:17][CH2:16][CH:15]([CH2:19][CH3:20])[C:14]1=[O:21])[CH2:8][CH2:9][CH3:10].[CH2:22](Br)C=C.CCOCC>CCCCCC>[CH2:19]([C:15]1([CH2:1][CH3:2])[CH2:16][CH2:17][CH2:18][C:13](=[CH:12][S:11][CH2:7][CH2:8][CH2:9][CH3:10])[C:14]1=[O:21])[CH:20]=[CH2:22]

참가 물질

6

반응물 4

HCID 3283Diethyl EtherHCID 7841Allyl bromideHCID 23665647Potassium tert-butoxideHCID 537663082-[(Butylthio)methylene]-6-ethylcyclohexanone

생성물 1

HCID 545033622-Allyl-6-[(butylthio)methylene]-2-ethylcyclohexanone

시약·촉매·용매 1

HCID 8058Hexane용매

실험 절차

To a well stirred solution of potassium tert-butoxide (17.95 g, 0.16 mole) in dry redistilled tert-butanol (160 ml) under nitrogen, 2-[(butylthio)methylene]6-ethylcylcohexanone (9.05 g, 0.04 mole), described in Example 3, is added slowly. The mixture is stirred at room temperature for 5 minutes and then chilled in an ice bath. Allyl bromide (21.8 g, 0.18 mole) is added rapidly to the chilled mixture. The mixture is then stirred at room temperature for 48 hr. Most of the solvent is then removed under reduced pressure and water (about 150 ml) is added. The aqueous solution is extracted with ether (3 ×). The combined ether extracts are washed with brine, dried (MgSO4) and concentrated to yield an oil. The oil is subjected to chromotography on silica gel (320 g) using 4% ether in hexane as eluant. Concentration of the eluate gives 2-allyl-6-[(butylthio)methylene]-2-ethylcyclohexanone, nmr(CDCl3) δ 0.85 (t, J=7, 3H), 2.85 (t, J=7, 2H), 4.80 - 6.0 (m, 3H), 7.5 (t, J=2, 1H).

후처리

  1. distillationredistilled tert-butanol (160 ml) under nitrogen
  2. additionis added slowly
  3. temperaturechilled in an ice bath
  4. stirringThe mixture is then stirred at room temperature for 48 hr
  5. customMost of the solvent is then removed under reduced pressure and water (about 150 ml)
  6. additionis added
  7. extractionThe aqueous solution is extracted with ether (3 ×)
  8. washThe combined ether extracts are washed with brine
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated
  11. customto yield an oil

출처 및 근거

ORD 기록
ord-cc9b0ea6a2494f1084cf3ac49292cdbb
출처 데이터셋
uspto-grants-1978_12
특허 번호
US04128560

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