4-Hexenoic acid → HCID 67754673, Verbindung

HRID 1769396Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1769396
[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.C(O)(=O)CCC=CC>>[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 3

HCID 1013844-Hexenoic acidHCID 168937Lithium hydroxide, monohydrateHCID 86748395HCID 86748395, Verbindung

Produkt 1

HCID 67754673HCID 67754673, Verbindung

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 (0.35g) and 0.05 g of LiOH-H2O in 9 ml 2:1 MeoH-H2O was heated at reflux for 4hours. 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 hexaneethyl 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 4hours
  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 hexaneethyl acetate:acetic acid)
  6. customto give 0.21 g of (E)-6-(1,3-dihydro-4- methoxycarbonylamino-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-4-methyl

Quellen und Nachweise

ORD-Eintrag
ord-333a3983f7044a91838dab429d3108a3
Quelldatensatz
uspto-grants-1995_01
Patentnummer
US05380879

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