Sodium hydride → HCID 178448628, Verbindung

HRID 340648

Reaktionsgleichung

Reaktionsgleichung von HRID 340648
[CH3:1][C:2]([OH:7])([CH3:6])[CH2:3][CH2:4][OH:5].[H-].[Na+].[CH2:10]([N:14]1[C:18]2[CH:19]=[N:20][CH:21]=[CH:22][C:17]=2[S:16]/[C:15]/1=[N:23]\[C:24](=[O:36])[C:25]1[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[CH:27][C:26]=1F)[CH2:11][CH2:12][CH3:13]>C1COCC1>[CH2:10]([N:14]1[C:18]2[CH:19]=[N:20][CH:21]=[CH:22][C:17]=2[S:16]/[C:15]/1=[N:23]\[C:24](=[O:36])[C:25]1[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[CH:27][C:26]=1[O:5][CH2:4][CH2:3][C:2]([OH:7])([CH3:6])[CH3:1])[CH2:11][CH2:12][CH3:13]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 247470IsopentyldiolHCID 178448621HCID 178448621, Verbindung

Produkt 1

HCID 178448628HCID 178448628, VerbindungAusbeute 90,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
2.5 °C

Versuchsvorschrift

3-Methylbutane-1,3-diol (42 mg, 0.4 mmol) in THF (1 mL) was treated with NaH (60%) (16 mg, 0.4 mmol) at room temperature for 20 min. To the above mixture, which was cooled to 0-5° C., was added the product from Example 20B (80 mg, 0.2 mmol) in THF (1 mL). After 20 min. the reaction mixture was quenched with saturated aqueous NaHCO3 (20 mL) and extracted with ethyl acetate (2×30 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 0-100% ethyl acetate in hexanes) to afford 87 mg (90%) of the title compound. 1H NMR (500 MHz, CDCl3) δ ppm 1.04 (t, J=7.32 Hz, 3H) 1.36 (s, 6H) 1.47-1.55 (m, 2H) 1.88-1.96 (m, 2H) 2.13 (t, J=5.80 Hz, 2H) 4.35 (t, J=5.80 Hz, 2H) 4.54 (t, J=7.63 Hz, 2H) 5.12 (brs, 1H) 7.11 (d, J=8.54 Hz, 1H) 7.61 (d, J=5.19 Hz, 1H) 7.74 (dd, J=8.54, 2.14 Hz, 1H) 8.49 (d, J=5.19 Hz, 1H) 8.68 (s, 1H) 8.72 (s, 1H); MS (ESI+) m/z 482 (M+H)+.

Aufarbeitung

  1. customAfter 20 min. the reaction mixture was quenched with saturated aqueous NaHCO3 (20 mL)
  2. extractionextracted with ethyl acetate (2×30 mL)
  3. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-4fbaf80223a743fe9d8a03d24f29aea6
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895592B2

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