Imidazole → (S)-3-(tert-butyldiphenylsilyloxy)dihydrofuran-2(3H)-one

HRID 1797857Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1797857
[OH:1][C@H:2]1[CH2:6][CH2:5][O:4][C:3]1=[O:7].N1C=CN=C1.C1COCC1.[Si:18](Cl)([C:31]([CH3:34])([CH3:33])[CH3:32])([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CC(OC)(C)C>[Si:18]([O:1][C@H:2]1[CH2:6][CH2:5][O:4][C:3]1=[O:7])([C:31]([CH3:34])([CH3:33])[CH3:32])([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

6

Edukt 4

HCID 795ImidazoleHCID 8028TetrahydrofuranHCID 94078tert-ButyldiphenylchlorosilaneHCID 3578532-Hydroxy-gamma-butyrolactone, (2S)-

Produkt 1

HCID 11739330(S)-3-(tert-butyldiphenylsilyloxy)dihydrofuran-2(3H)-oneAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 15413tert-Butyl methyl etherLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a stirred solution of (S)-3-hydroxydihydrofuran-2(3H)-one (5.24 g, 51.4 mmol), imidazole (3.8 g, 56 mmol), and THF (70 mL) at 0° C., under N2, was added t-butyldiphenylsilyl chloride (11.8 g, 43 mmol) dropwise. The mixture was stirred at 0° C. for 6 hours. TBME (150 mL) was added and the solution was washed with water (2×100 mL), brine (100 mL), dried over sodium sulfate, filtered, and evaporated to dryness under reduced pressure to afford (S)-3-(tert-butyldiphenylsilyloxy)dihydrofuran-2(3H)-one (13.9 g, 95%) as a slightly yellow oil. 1H-NMR (400 MHz, CDCl3) δ 7.84-0.82 (m, 2H), 7.73-7.71 (m, 2H), 7.50-7.40 (m, 6H), 4.41-4.31 (m, 2H), 4.06-4.00 (m, 1H), 2.29-2.19 (m, 2H), 1.10 (s, 9H).

Aufarbeitung

  1. washthe solution was washed with water (2×100 mL), brine (100 mL)
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated to dryness under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-53f0fb12ffbf4fa69ef6c7f18398ed4e
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08343763B2

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