Lithium hydroxide, monohydrate → HCID 67754673, Verbindung

HRID 1756623Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1756623
[CH3:1][O:2][C:3]([NH:5][C:6]1[C:14]([CH2:15]/[CH:16]=[C:17](\[CH3:24])/[CH2:18][CH2:19][C:20]([O:22]C)=[O:21])=[C:13]([O:25][CH3:26])[C:12]([CH3:27])=[C:11]2[C:7]=1[C:8](=[O:28])[O:9][CH2:10]2)=[O:4].O[Li].O>CO.O>[CH3:1][O:2][C:3]([NH:5][C:6]1[C:14]([CH2:15]/[CH:16]=[C:17](\[CH3:24])/[CH2:18][CH2:19][C:20]([OH:22])=[O:21])=[C:13]([O:25][CH3:26])[C:12]([CH3:27])=[C:11]2[C:7]=1[C:8](=[O:28])[O:9][CH2:10]2)=[O:4]

Komponenten

4

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 86748395HCID 86748395, Verbindung

Produkt 1

HCID 67754673HCID 67754673, VerbindungAusbeute 62,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 22242641Methanol--water (1/1)Lösungsmittel

Versuchsvorschrift

A solution of methyl (E)-6-(1,3-dihydro-4-isocyanato-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-4-methyl-4-hexenoate (1.0 g) in 10 ml methanol was heated to reflux for 4 hours and then evaporated to dryness. The residue was recrystallized from acetone/hexane to give 0.41 g of methyl (E)-6-(1,3-dihydro-4-methoxycarbonylamino-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-4-methyl-4-hexenoate. The ester (0.35 g) and 0.05 g of LiOH-H2O in 9 ml 2:1 MeOH-H2O was heated at reflux for 4 hours. The mixture was acidified, extracted with ethyl acetate, and the organic layer was dried over MgSO4. The organic layer was concentrated and the residue was further purified by silica gel chromatography (eluant 60:40:2 hexane:ethyl acetate:acetic acid) to give 0.21 g of (E)-6-(1,3-dihydro-4-methoxycarbonylamino-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-4-methyl-4-hexenoic acid, mp 155°-158° C.

Aufarbeitung

  1. temperatureat reflux for 4 hours
  2. extractionextracted with ethyl acetate
  3. dry with materialthe organic layer was dried over MgSO4
  4. concentrationThe organic layer was concentrated
  5. customthe residue was further purified by silica gel chromatography (eluant 60:40:2 hexane:ethyl acetate:acetic acid)

Quellen und Nachweise

ORD-Eintrag
ord-c84fe8a57f8440d1a86fa41584dc0636
Quelldatensatz
uspto-grants-1995_08
Patentnummer
US05441953

Notizen zur Reaktion

Wird geladen…