Sodium ethoxide → HCID 21928991, compound

HRID 1243855Notes

Reaction equation

HRID 1243855 reaction equation
O=[C:2]1[CH:7]=[CH:6][C:5]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:4][CH:3]1[NH:20][CH:21]=[CH:22][C:23]([O:25][CH2:26][CH3:27])=[O:24].[O-]CC.[Na+]>C(O)C>[C:8]1([C:5]2([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:4][C:3]3[NH:20][CH:21]=[C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:2]=3[CH:7]=[CH:6]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 69594764HCID 69594764, compound

Product 1

HCID 21928991HCID 21928991, compoundYield 4.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

0.3 g of ethyl 3-(2-oxo-5,5-diphenylcyclohex-3-enylamino)acrylate is dissolved in 6 cm3 of ethanol. The solution obtained is cooled to a temperature in the region of 0° C. 2 cm3 of sodium ethoxide solution (obtained from 0.23 g of sodium in 20 cm3 of ethanol) are added to the preceding solution at a temperature of between 0 and 5° C. After warming to a temperature in the region of 20° C., the resulting mixture is stirred for about 18 hours. About ten grams of crushed ice are then added to the reaction mixture and this mixture is then concentrated under reduced pressure (13 kPa) to half its volume. The mixture thus obtained is extracted five times with diethyl ether (three times 100 cm3, twice 50 cm3). The combined organic phases are successively washed with 100 cm3 and then 50 cm3 of saturated aqueous sodium chloride solution and then dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (13 kPa). The residue is purified by flash chromatography on a column of silica (eluent: cyclohexane/ethyl acetate (85/15 by volume)]. 0.013 g of ethyl 6,6-diphenyl-6,7-dihydro-1H-indole-3-carboxylate is thus obtained in the form of a yellow solid, the characteristics of which are as follows:

Workup

  1. customThe solution obtained
  2. temperatureAfter warming to a temperature in the region of 20° C.
  3. concentrationthis mixture is then concentrated under reduced pressure (13 kPa) to half its volume
  4. customThe mixture thus obtained
  5. extractionis extracted five times with diethyl ether (three times 100 cm3, twice 50 cm3)
  6. washThe combined organic phases are successively washed with 100 cm3
  7. dry with material50 cm3 of saturated aqueous sodium chloride solution and then dried over magnesium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated to dryness under reduced pressure (13 kPa)
  10. customThe residue is purified by flash chromatography on a column of silica (eluent

Sources & evidence

ORD record
ord-835c7723e56e415a9114d0d7827784af
Source dataset
uspto-grants-2006_10
Patent number
US07119115B2

Reaction notes

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