Diethyl Ether → Stannane, trimethyl(4-methylphenyl)-

HRID 1033412

反応式

HRID 1033412 の反応式
[C:1]1([CH3:9])[CH:6]=[CH:5][C:4]([Mg]Br)=[CH:3][CH:2]=1.C(OCC)C.[CH3:15][Sn:16](Cl)([CH3:18])[CH3:17].[Cl-].[NH4+].CC1C=CC(C2C=CC(C)=CC=2)=CC=1>O1CCCC1.O>[CH3:9][C:1]1[CH:6]=[CH:5][C:4]([Sn:16]([CH3:18])([CH3:17])[CH3:15])=[CH:3][CH:2]=1

参加物

8

反応物 5

HCID 3283Diethyl EtherHCID 11941Di-p-tolylHCID 14016Trimethyltin chlorideHCID 25517Ammonium Chloride2 回HCID 178418370HCID 178418370、化合物

生成物 1

HCID 617834Stannane, trimethyl(4-methylphenyl)-収率 100%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

41.4L of 1.0 M p-tolylmagnesium bromide in diethyl ether (41.4 mol) was added dropwise, maintaining the temperature below -5° C., over 4 hours to a solution of 546 g (2.79 mol) of trimethyltin chloride in tetrahydrofuran (4L) under nitrogen at -10 C. The suspension was allowed to warm slowly to room temperature over 12 h then saturated ammonium chloride solution (1L) was added followed by sufficient water (approximately 1L) to dissolve the precipitate. The solution was extracted with ether-hexane (1:1) (1×4L, 3×2L). The combined organic phases were washed with brine, dried over magnesium sulfate and the solvents removed under vacuum. Purification by flash chromatography on silica gel eluting with hexane/ethyl acetate (95:5) gave a pale yellow oil containing white crystals of 4,4'-dimethylbiphenyl which were removed by filtration to leave 711.3 g (100%) of product. 1H NMR (300MHz,CDCl3): 0.30 (s,9H), 2.34 (s,3 H), 7.19 (d,7.7Hz,2H), 7.40 (d,7.7Hz,2H).

後処理

  1. temperaturemaintaining the temperature below -5° C.
  2. dissolutionto dissolve the precipitate
  3. extractionThe solution was extracted with ether-hexane (1:1) (1×4L, 3×2L)
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customthe solvents removed under vacuum
  7. customPurification by flash chromatography on silica gel eluting with hexane/ethyl acetate (95:5)
  8. customgave a pale yellow oil
  9. customwere removed by filtration

出典と根拠

ORDレコード
ord-ae282d93c464437792eb653292e5b568
出典データセット
uspto-grants-1994_05
特許番号
US05310737

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