tert-Butanol → 2-Allyl-6-[(butylthio)methylene]-2-ethylcyclohexanone

HRID 1438915ノート

反応式

HRID 1438915 の反応式
[CH3:1][C:2](C)([O-])C.[K+].[C:7](O)(C)(C)C.[CH2:12]([S:16][CH:17]=[C:18]1[CH2:23][CH2:22][CH2:21][CH:20]([CH2:24][CH3:25])[C:19]1=[O:26])[CH2:13][CH2:14][CH3:15].C(Br)C=C>CCCCCC.CCOCC>[CH2:24]([C:20]1([CH2:1][CH3:2])[CH2:21][CH2:22][CH2:23][C:18](=[CH:17][S:16][CH2:12][CH2:13][CH2:14][CH3:15])[C:19]1=[O:26])[CH:25]=[CH2:7]

参加物

7

反応物 4

HCID 6386tert-ButanolHCID 7841Allyl bromideHCID 23665647Potassium tert-butoxideHCID 537663082-[(Butylthio)methylene]-6-ethylcyclohexanone

生成物 1

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

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8058Hexane溶媒

実験手順

To a well stirred solution of potassium tert-butoxide (17.95 g, 0.16 mole) in dry redistilled tert-butanol (160 ml) 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 x). The combined ether extracts are washed with brine, dried (MgSO4) and concentrated to yield 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).

後処理

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

出典と根拠

ORDレコード
ord-ad607d2a537d4cc48bda80b8e410ab35
出典データセット
uspto-grants-1977_11
特許番号
US04057559

反応ノート

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