Pyridine → 2-Tert-butoxycarbonyloxyimino-2-(1-naphthyl)acetonitrile

HRID 2082993

Reaktionsgleichung

Reaktionsgleichung von HRID 2082993
[C:1]([OH:5])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.Cl[C:13]([O:15][N:16]=[C:17]([C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1)[C:18]#[N:19])=[O:14]>C1(C)C=CC=CC=1>[C:1]([O:5][C:13]([O:15][N:16]=[C:17]([C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1)[C:18]#[N:19])=[O:14])([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 6386tert-ButanolHCID 543473962-Chlorocarbonyloxyimino-2-(1-naphthyl)acetonitrile

Produkt 1

HCID 537899872-Tert-butoxycarbonyloxyimino-2-(1-naphthyl)acetonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

The mixture was stirred for 3 hours at the same temperature and allowed to stand overnight. A solution of tert-butyl alcohol (11.1 g.) and pyridine (12 ml.) in toluene (20 ml.) was added dropwise, under ice-cooling, to the resultant mixture containing 2-chlorocarbonyloxyimino-2-(1-naphthyl)-acetonitrile. The mixture was stirred for 6 hours at the same temperature and allowed to stand overnight. The reaction mixture was then washed with water, 1N hydrochloric acid, water, a sodium bicarbonate aqueous solution and water, and dried over magnesium sulfate. The solution was concentrated under reduced pressure and n-hexane and methanol were added to the residue. The mixture was allowed to stand in a refrigerator and the precipitated crystals were collected by filtration and recrystallized twice from methanol to give 2-tert-butoxycarbonyloxyimino-2-(1-naphthyl)acetonitrile (3.3 g.), mp 90° to 92° C.

Aufarbeitung

  1. waitto stand overnight
  2. stirringThe mixture was stirred for 6 hours at the same temperature
  3. waitto stand overnight
  4. washThe reaction mixture was then washed with water, 1N hydrochloric acid, water
  5. dry with materiala sodium bicarbonate aqueous solution and water, and dried over magnesium sulfate
  6. concentrationThe solution was concentrated under reduced pressure and n-hexane and methanol
  7. additionwere added to the residue
  8. filtrationthe precipitated crystals were collected by filtration
  9. customrecrystallized twice from methanol

Quellen und Nachweise

ORD-Eintrag
ord-ab5798a97bcf4fb898f6d43e4338dd25
Quelldatensatz
uspto-grants-1978_04
Patentnummer
US04083848

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