Sodium Carbonate → HCID 54328351, compound

HRID 2226530Notes

Reaction equation

HRID 2226530 reaction equation
C(O)(=O)C=CC(O)=O.[NH:9]1[CH2:13][CH:12]=[CH:11][CH2:10]1.C(=O)([O-])[O-].[Na+].[Na+].[O:20]1[CH:22]2[CH2:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:29]=3[CH:21]12.[OH-].[Na+]>O>[N:9]1([C@@H:21]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH2:23][C@H:22]2[OH:20])[CH2:13][CH:12]=[CH:11][CH2:10]1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 92838Indene oxideHCID 86187054HCID 86187054, compound

Product 1

HCID 54328351HCID 54328351, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
70 °C

Procedure

A solution of 10 g of 2,5-dihydro-1H-pyrrole (2-butenedioate) and 6 g of sodium carbonate in 20 ml of water was added at 20° C. to a solution of 7.4 g of 1a,6a-dihydro-6H-indeno [1,2-b] oxirene in 5 ml of water and the mixture was heated at 70° C. for 4 hours and allowed to cool to room temperature. 15 ml of sodium hydroxide solution were added and the mixture was extracted with ethyl acetate. The organic phase was dried and evaporated to dryness under reduced pressure to obtain 8.62 g of raw product. The latter was chromatographed over silica and eluted with a 98-2 ethyl acetate-triethylamine mixtures to obtain the desired product.

Workup

  1. temperatureto cool to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. customThe organic phase was dried
  4. customevaporated to dryness under reduced pressure
  5. customto obtain 8.62 g of raw product
  6. customThe latter was chromatographed over silica
  7. washeluted with a 98-2 ethyl acetate-triethylamine mixtures

Sources & evidence

ORD record
ord-c2cd97df948c4e909bf8005af3da0e60
Source dataset
uspto-grants-1994_09
Patent number
US05348971

Reaction notes

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