Diazomethane → HCID 13076873, Verbindung

HRID 1438727Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1438727
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]2[O:6][C@H:7]([C:16]([OH:18])=[O:17])[O:8][C@H:9]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:4]=2[CH:3]=1.[N+](=[CH2:23])=[N-]>CCOCC>[Cl:1][C:2]1[CH:20]=[CH:19][C:5]2[O:6][C@H:7]([C:16]([O:18][CH3:23])=[O:17])[O:8][C@H:9]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:4]=2[CH:3]=1

Komponenten

4

Edukt 2

HCID 9550Diazomethane2×HCID 12812406HCID 12812406, Verbindung

Produkt 1

HCID 13076873HCID 13076873, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To an ether solution of cis-6-chloro-4-phenyl-1,3-benzodioxan-2-carboxylic acid (2.14 g, 7.36 mmoles), chilled in an ice bath, was added an ethereal solution of diazomethane until the yellow color of the diazomethane was no longer discharged. The solution was stirred in the ice bath for 10 minutes at room temp. for 10 minutes, and finally at 35° for 15 minutes. The ether solution was washed with dil.NaHCO3 solution (2 portions), water (2 portions), and saturated brine (1 portion), and dried over anhydrous Na2SO4. The solvent was evaporated to yield a solid which was recrystallized from benzene-Skellysolve B (essentially n-hexane). The yield was 1.71 g (76%); m.p. 129.5°-131°. NMR (CDCl3), β6.6 (d, 1H, C(5)H, cis); 5.65 ppm (s, 1H, C(2)H, cis).

Aufarbeitung

  1. washThe ether solution was washed with dil
  2. dry with materialNaHCO3 solution (2 portions), water (2 portions), and saturated brine (1 portion), and dried over anhydrous Na2SO4
  3. customThe solvent was evaporated
  4. customto yield a solid which
  5. customwas recrystallized from benzene-Skellysolve B (essentially n-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-029b35d05f16401695956a36d38207da
Quelldatensatz
uspto-grants-1977_11
Patentnummer
US04056540

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