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Sodium hydride → HCID 18704224, Verbindung

HRID 2288296
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2288296
[H-].[Na+].[O:3]=[C:4]1[N:8]([C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[C:11]([C:17]([F:20])([F:19])[F:18])[CH:10]=2)[C:7](=[O:21])[C:6]2([CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[NH:5]1.[H][H].C[Si](C)(C)[O:31][CH2:32][CH2:33][CH2:34][CH2:35]I>CN(C)C=O>[O:3]=[C:4]1[N:8]([C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[C:11]([C:17]([F:20])([F:18])[F:19])[CH:10]=2)[C:7](=[O:21])[C:6]2([CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[N:5]1[CH2:35][CH2:34][CH2:33][CH2:32][OH:31]
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Komponenten

6

Edukt 4

HCID 24758Sodium hydrideHCID 10978586Silane, (4-iodobutoxy)trimethyl-HCID 18704219HCID 18704219, VerbindungHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 18704224HCID 18704224, VerbindungAusbeute 76,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Versuchsvorschrift

28 mg of 50% sodium hydride and 3 ml of dimethylformamide are introduced, agitation is carried out at ambient temperature for 5 minutes, 170 mg of the product obtained in Stage 3 above is added and the whole is left under agitation for 20 minutes until the release of hydrogen has stopped. 202 mg of O-trimethylsilyl-4-iodo-n-butanol is then added and the reaction medium is left under agitation for 2 hours. After hydrolysis using saturated ammonium chloride, extraction is carried out with ethyl acetate. The organic phases are combined, washed with water, dried, filtered and concentrated. The residue is solubilized in 10 ml of methanol and 0.5 ml of 2N hydrochloric acid is added. After agitation for 5 minutes, the solution is neutralized by the addition of saturated sodium hydrogen carbonate and extraction is carried out with ethyl acetate. The organic phases are combined, dried, filtered and concentrated. After chromatography on silica eluting with methylene chloride-acetone: 9-1, 158 mg of expected product (white solid) is obtained. M.p.=145° C.

Aufarbeitung

  1. waitthe reaction medium is left under agitation for 2 hours
  2. customAfter hydrolysis
  3. extractionammonium chloride, extraction
  4. washwashed with water
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. addition0.5 ml of 2N hydrochloric acid is added
  9. waitAfter agitation for 5 minutes
  10. additionthe solution is neutralized by the addition of saturated sodium hydrogen carbonate and extraction
  11. customdried
  12. filtrationfiltered
  13. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-6118d6b7654447e183a59545e74e62c1
Quelldatensatz
uspto-grants-2000_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06087509

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