Reaktion #65220

ord-39327534f9f6407da25e5ec506d843ce

Reaktionsgleichung

CC(C)(C)c1cc(C(=O)c2cc3c(cc2O)CCC3)cc(C(C)(C)C)c1O
5- (3,5-di-tert-butyl-4-hydroxybenzoyl)-6-hydroxyindan
CCOC(=O)CC(=O)OCC
diethyl malonate
C1CCC2=NCCCN2CC1
DBU
→
CCOC(=O)c1c(-c2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)c2cc3c(cc2oc1=O)CCC3
ethyl 4-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-oxo-2,6,7,8-tetrahydrocyclopenta [g] [1]benzopyran-3-carboxylate
Ausbeute 87.8%

Edukte

CC(C)(C)c1cc(C(=O)c2cc3c(cc2O)CCC3)cc(C(C)(C)C)c1O
5- (3,5-di-tert-butyl-4-hydroxybenzoyl)-6-hydroxyindan
CCOC(=O)CC(=O)OCC
diethyl malonate
C1CCC2=NCCCN2CC1
DBU

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Temperaturwas heated at 160°-170° C. for 2 hours
  2. 2
    TemperaturAfter cooling
  3. 3
    Filtrationthe resulting crystals were collected by filtration
  4. 4
    Waschenwashed with ethanol

Vorschrift

A mixture of 5- (3,5-di-tert-butyl-4-hydroxybenzoyl)-6-hydroxyindan (2.8 g), diethyl malonate (3.6 g) and DBU (0.12 ml) was heated at 160°-170° C. for 2 hours. After cooling, the resulting crystals were collected by filtration and washed with ethanol to give ethyl 4-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-oxo-2,6,7,8-tetrahydrocyclopenta [g] [1]benzopyran-3-carboxylate (3.1 g, 87.8%). Recrystallization from ethanol gave colorless prisms, m.p. 208°-209° C.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05418239uspto-grants-1995_05