1-Bromo-1-methylcyclohexane → ethyl (2Z)-2-(1-methylcyclohexyl)oxyimino-3-oxobutanoate

HRID 1194878ノート

反応式

HRID 1194878 の反応式
[OH:1]/[N:2]=[C:3](/[C:9](=[O:11])[CH3:10])\[C:4]([O:6][CH2:7][CH3:8])=[O:5].Br[C:13]1([CH3:19])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1>O1CCOCC1.FC(F)(F)S([O-])(=O)=O.[Ag+]>[CH3:19][C:13]1([O:1]/[N:2]=[C:3](/[C:9](=[O:11])[CH3:10])\[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

参加物

5

反応物 2

HCID 125021291-Bromo-1-methylcyclohexaneHCID 178472876HCID 178472876、化合物

生成物 1

HCID 14864970ethyl (2Z)-2-(1-methylcyclohexyl)oxyimino-3-oxobutanoate収率 69%

試薬・触媒・溶媒 2

HCID 76223Silver(I) trifluoromethanesulfonate触媒HCID 312751,4-Dioxane溶媒

実験手順

Ethyl (Z)-2-hydroxyimino-3-oxobutyrate (3.18 g, 20 mmol) and 1-bromo-1-methylcyclohexane (3.54 g, 20 mmol) in dry dioxane (15 ml) were stirred together in the dark and silver trifluoromethanesulphonate (5.13 g, 20 mmol) was added portionwise over 4 h. After a total of 100 h the mixture was filtered through Kieselguhr and the residue was washed well with dioxane. The filtrate was evaporated in vacuo, toluene was added and evaporated in vacuo and the residual oil was dissolved in ethyl acetate and washed with dilute aqueous NaHCO3, followed by water and brine. Ater drying (MgS4) the ethyl acetate was evaporated in vacuo and the residual oil was chromatographed on silica gel, to give the title compound as a yellow oil (3.49 g; 69%); νmax (CH2Cl2) 2945, 1740, 1685, 1370, 1320, 1235, 1070 and 1005 cm-1 ; δH (60 MHz, CDCl3) 1.35 (6H, s superimposed on t), 1.4-2.0 (10H, m), 2.37 (3H, s), 4.55 (2H, q, J 7 Hz).

後処理

  1. additionwas added portionwise over 4 h
  2. filtrationAfter a total of 100 h the mixture was filtered through Kieselguhr
  3. washthe residue was washed well with dioxane
  4. customThe filtrate was evaporated in vacuo, toluene
  5. additionwas added
  6. customevaporated in vacuo
  7. dissolutionthe residual oil was dissolved in ethyl acetate
  8. washwashed with dilute aqueous NaHCO3
  9. dry with materialAter drying (MgS4) the ethyl acetate
  10. customwas evaporated in vacuo
  11. customthe residual oil was chromatographed on silica gel

出典と根拠

ORDレコード
ord-40b1f18248e34153bba737bc69091074
出典データセット
uspto-grants-1989_03
特許番号
US04816452

反応ノート

読み込み中…