Tetrahydrofuran → HCID 67270703, Verbindung

HRID 1039730

Reaktionsgleichung

Reaktionsgleichung von HRID 1039730
[Si:1]([O:8][C@H:9]([CH2:18][O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])/[CH:10]=[N:11]/[S@:12]([C:14]([CH3:17])([CH3:16])[CH3:15])=[O:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:27]([Li])([CH3:30])([CH3:29])[CH3:28].C1C[O:35][CH2:34]C1>>[Si:1]([O:8][C@H:9]([CH2:18][O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:21])[CH3:22])[C@@H:10]([NH:11][S@:12]([C:14]([CH3:15])([CH3:16])[CH3:17])=[O:13])[CH2:28][CH:27]1[CH2:30][CH2:34][O:35][CH2:29]1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Komponenten

4

Edukt 3

HCID 8028TetrahydrofuranHCID 44239381(NE,S)-N-[(2S)-2,3-bis[[tert-butyl(dimethyl)silyl]oxy]propylidene]-2-methylpropane-2-sulfinamideHCID 178418306HCID 178418306, Verbindung

Produkt 1

HCID 67270703HCID 67270703, Verbindung

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

A solution of azeotropically dried (S,E)-N-((S)-2,3-bis(tert-butyldimethylsilyloxy)propylidene)-2-methylpropane-2-sulfinamide (2.3 g, 5 mmol) and 3-(iodomethyl)-THF (1 g, 7 mmol) in dry THF (10 mL) was brought to −78° C. followed by the dropwise addition of tert-butyllithium (6 mL, 11 mmol). A white precipitate was formed. The resulting solution was stirred at −78° C. for 40 min, quenched with sat NH4Cl and extracted with EtOAc. The combined organics were washed with brine, dried over Na2SO4, filtered, concentrated, and chromatographed on silica gel using 0-5% EtOAc/hexanes to afford a colorless oil as (S)-N-((2S,3S)-3,4-bis(tert-butyldimethylsilyloxy)-1-(tetrahydrofuran-3-yl)butan-2-yl)-2-methylpropane-2-sulfinamide.

Aufarbeitung

  1. customwas brought to −78° C.
  2. customA white precipitate was formed
  3. customquenched with sat NH4Cl
  4. extractionextracted with EtOAc
  5. washThe combined organics were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customchromatographed on silica gel using 0-5% EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-5854fd72d51041fd9d5ce3afe3f767a3
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08552181B2

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