Imidazole → 6-(2-tert-butyidimethylsilyloxyphenyl)thio-2,2,3-trimethyl-2H-benzo[b]pyran

HRID 1416185Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1416185
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C:9]1[CH:21]=[CH:20][C:12]2[O:13][C:14]([CH3:19])([CH3:18])[C:15]([CH3:17])=[CH:16][C:11]=2[CH:10]=1.N1C=CN=C1.[Si:27](Cl)([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28].O>CN(C)C=O>[Si:27]([O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C:9]1[CH:21]=[CH:20][C:12]2[O:13][C:14]([CH3:18])([CH3:19])[C:15]([CH3:17])=[CH:16][C:11]=2[CH:10]=1)([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28]

Komponenten

6

Edukt 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 187828886-(2-hydroxyphenyl)thio-2,2,3-trimethyl-2H-benzo[b]pyran

Produkt 1

HCID 543808176-(2-tert-butyidimethylsilyloxyphenyl)thio-2,2,3-trimethyl-2H-benzo[b]pyranAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

6-(2-hydroxyphenyl)thio-2,2,3-trimethyl-2H-benzo[b]pyran (1.1 g) (see Preparation 10) was dissolved in dry dimethylformamide (2 ml) and imidazole (0.55 g) and tert-butyldimethylsilyl chloride (0.61 g) were added. The flask was fitted with a calcium chloride drying tube and the mixture stirred at 40° C. for 90 minutes. Water was added and the mixture was extracted with diethyl ether. The organic extract was washed with aqueous sodium hydrogen carbonate solution (×2), dried (anhydrous sodium sulphate), the solvent removed under reduced pressure and the crude product was chromatographed on silica using 4:1 hexane: dichloromethane as the eluent to yield 6-(2-tert-butyidimethylsilyloxyphenyl)thio-2,2,3-trimethyl-2H-benzo[b]pyran (1.43 g) as an oil.

Aufarbeitung

  1. customThe flask was fitted with a calcium chloride drying tube
  2. extractionthe mixture was extracted with diethyl ether
  3. extractionThe organic extract
  4. washwas washed with aqueous sodium hydrogen carbonate solution (×2)
  5. dry with materialdried (anhydrous sodium sulphate)
  6. customthe solvent removed under reduced pressure
  7. customthe crude product was chromatographed on silica using 4:1 hexane

Quellen und Nachweise

ORD-Eintrag
ord-c45637a7b0184063b4263a63cd15881b
Quelldatensatz
uspto-grants-1999_06
Patentnummer
US05912244

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