Diethyl Malonate → Ethyl 4-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-oxo-2,6,7,8-tetrahydrocyclopenta[g][1]benzopyran-3-carboxylate

HRID 36942Notes

Reaction equation

HRID 36942 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:20]=[C:21]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:22]=1[OH:23])[C:8]([C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][C:18]=1[OH:19])[CH2:15][CH2:14][CH2:13]2)=O)([CH3:4])([CH3:3])[CH3:2].[C:28](OCC)(=[O:35])[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31].C1CCN2C(=NCCC2)CC1>>[C:24]([C:21]1[CH:20]=[C:7]([C:8]2[C:10]3[CH:11]=[C:12]4[CH2:13][CH2:14][CH2:15][C:16]4=[CH:17][C:18]=3[O:19][C:28](=[O:35])[C:29]=2[C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:22]=1[OH:23])([CH3:26])([CH3:27])[CH3:25]

Participants

4

Reactant 3

HCID 7761Diethyl MalonateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 19936580HCID 19936580, compound

Product 1

HCID 19782167Ethyl 4-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-oxo-2,6,7,8-tetrahydrocyclopenta[g][1]benzopyran-3-carboxylateYield 87.8%

Procedure

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.

Workup

  1. temperaturewas heated at 160°-170° C. for 2 hours
  2. temperatureAfter cooling
  3. filtrationthe resulting crystals were collected by filtration
  4. washwashed with ethanol

Sources & evidence

ORD record
ord-39327534f9f6407da25e5ec506d843ce
Source dataset
uspto-grants-1995_05
Patent number
US05418239

Reaction notes

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