Dibenzofuran → Dibenzofuran, 4-methyl-

HRID 964565

Reaktionsgleichung

Reaktionsgleichung von HRID 964565
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH2:14]([Li])CCC.S(OC)(OC)(=O)=O.[Cl-].[NH4+]>C1COCC1>[CH3:14][C:4]1[C:5]2[O:6][C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=3[C:9]=2[CH:1]=[CH:2][CH:3]=1

Komponenten

6

Edukt 4

HCID 568DibenzofuranHCID 6497Dimethyl SulfateHCID 25517Ammonium ChlorideHCID 178418339Butyllithium

Produkt 1

HCID 43489Dibenzofuran, 4-methyl-Ausbeute 100,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Dibenzofuran (26.94 g, 160 mmol) was dissolved in dry THF (500 ml) and cooled to -78° C. n-Butyl lithium (1.6M in hexane, 200 ml, 320 mmol) was added in portions over 30 mins. and the solution was allowed to warm to room temperature over 2.5 hours. The solution was recooled to -70° C. and a mixture of dimethyl sulphate (32 ml, 340 mmol) in dry THF (100 ml) was added dropwise. Once the addition was complete, the reaction was allowed to warm to room temperature, stirred for 18 hours and poured onto saturated ammonium chloride solution (400 ml). The phases were separated and the aqueous extracted twice with ether. The combined organic phases were dried (MgSO4) and evaporated in vacuo. Chromatography on silica (eluting with 40-60 petrol) gave the pure product as a clear oil (29.2 g, 100%) δH [2H6 ]-DMSO 8.1 (1H, d), 7.9 (1H, d), 7.7 (1H, d),7.5 (1H, t), 7.4 (1H, t), 7.25 (2H, m), 2.55 (3H, s).

Aufarbeitung

  1. additionwas added in portions over 30 mins
  2. customwas recooled to -70° C.
  3. additionwas added dropwise
  4. additionOnce the addition
  5. temperatureto warm to room temperature
  6. customThe phases were separated
  7. extractionthe aqueous extracted twice with ether
  8. dry with materialThe combined organic phases were dried (MgSO4)
  9. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-31779468f8784f4498be2fec604b723d
Quelldatensatz
uspto-grants-1998_06
Patentnummer
US05770598

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