Imidazole → 6-(4-tert-butyldimethylsilyloxyphenyl)thio-2,2,3-trimethyl-2H-benzo[b]pyran

HRID 1420760

Reaktionsgleichung

Reaktionsgleichung von HRID 1420760
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:21]=[CH:20][C:12]3[O:13][C:14]([CH3:19])([CH3:18])[C:15]([CH3:17])=[CH:16][C:11]=3[CH:10]=2)=[CH:4][CH:3]=1.N1C=CN=C1.[Si:27](Cl)([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28]>CN(C)C=O>[Si:27]([O:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][C:9]2[CH:21]=[CH:20][C:12]3[O:13][C:14]([CH3:18])([CH3:19])[C:15]([CH3:17])=[CH:16][C:11]=3[CH:10]=2)=[CH:6][CH:7]=1)([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28]

Komponenten

5

Edukt 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 187828866-(4-hydroxyphenyl)thio-2,2,3-trimethyl-2H-benzo[b]pyran

Produkt 1

HCID 538369336-(4-tert-butyldimethylsilyloxyphenyl)thio-2,2,3-trimethyl-2H-benzo[b]pyranAusbeute 83,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

6-(4-Hydroxyphenyl)thio-2,2,3-trimethyl-2H-benzo[b]pyran (5.799 g) (see Preparation 8) was dissolved in dry dimethylformamide (12 ml) and imidazole (2.768 g) and tert-butyidimethylsilyl chloride (2.923 g) were added. The flask was fitted with a calcium chloride drying tube and the mixture was stirred at 40° C. for 18 hours. The solvent was then removed under reduced pressure and the residue was partitioned between aqueous sodium bicarbonate solution and dichloromethane. The organic layer was dried (anhydrous sodium sulphate), the solvent removed under reduced pressure and the crude product chromatographed on silica using 1:1 hexane:dichloromethane as the eluent to yield 6-(4-tert-butyldimethylsilyloxyphenyl)thio-2,2,3-trimethyl-2H-benzo[b]pyran (6.681 g) as an oil. LRMS m/z=413 (m+1)+.

Aufarbeitung

  1. customThe flask was fitted with a calcium chloride drying tube
  2. customThe solvent was then removed under reduced pressure
  3. customthe residue was partitioned between aqueous sodium bicarbonate solution and dichloromethane
  4. dry with materialThe organic layer was dried (anhydrous sodium sulphate)
  5. customthe solvent removed under reduced pressure
  6. customthe crude product chromatographed on silica using 1:1 hexane

Quellen und Nachweise

ORD-Eintrag
ord-408c0827a2524601a8ebf4509dfad1c4
Quelldatensatz
uspto-grants-2000_06
Patentnummer
US06071938

Verknüpfte Notizen

Wird geladen…