Diethyl Malonate → HCID 70448088, compound

HRID 1493296Notes

Reaction equation

HRID 1493296 reaction equation
[C:1]([O:9]CC)(=[O:8])[CH2:2][C:3](OCC)=O.[H-].[Na+].[CH3:14][O:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[CH:21]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]CBr)[CH:20]([C:36]1[CH:41]=[CH:40][C:39]([O:42]C)=[CH:38][CH:37]=1)[CH2:19]2>CN(C)C=O.O>[CH3:14][O:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[CH:21]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:3][CH2:2][C:1]([OH:9])=[O:8])[CH:20]([C:36]1[CH:41]=[CH:40][C:39]([OH:42])=[CH:38][CH:37]=1)[CH2:19]2

Participants

6

Reactant 3

HCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 70447080HCID 70447080, compound

Product 1

HCID 70448088HCID 70448088, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
50 °C

Procedure

A solution of diethyl malonate (0.64 g.) in dimethylformamide (10 ml.) was added to a stirred suspension of sodium hydride (0.14 g. of a 50% suspension in mineral oil) in dimethylformamide (10 ml.) which was maintained under an atmosphere of argon, and the mixture was stirred and heated to 50° C. for 5 minutes and then cooled to laboratory temperature. 10-[(1RS, 2RS)-5-Methoxy-2-p-methoxyphenylindan-1-yl]decyl bromide (1.2 g.) was added and the mixture was stirred at laboratory temperature for 16 hours and then diluted with water and extracted with diethyl ether. The extract was dried and evaporated to dryness and a solution of the residue (1.47 g.) in ethanol (10 ml.) was added dropwise to a stirred solution of potassium hydroxide (1.4 g.) in water (10 ml.) which was heated under reflux. The mixture was stirred and heated under reflux for 10 minutes, diluted with water and extracted with diethyl ether. The aqueous solution was acidified with concentrated aqueous hydrochloric acid and extracted with diethyl ether, and the extract was dried and evaporated to dryness. There was thus obtained as residue 12-[(1RS, 2RS)-5-methoxy-2-p-hydroxyphenylindan-1-yl]dodecanoic acid.

Workup

  1. temperaturecooled to laboratory temperature
  2. stirringthe mixture was stirred at laboratory temperature for 16 hours
  3. extractionextracted with diethyl ether
  4. customThe extract was dried
  5. customevaporated to dryness
  6. additiona solution of the residue (1.47 g.) in ethanol (10 ml.) was added dropwise to a stirred solution of potassium hydroxide (1.4 g.) in water (10 ml.) which
  7. temperaturewas heated
  8. temperatureunder reflux
  9. stirringThe mixture was stirred
  10. temperatureheated
  11. temperatureunder reflux for 10 minutes
  12. additiondiluted with water
  13. extractionextracted with diethyl ether
  14. extractionextracted with diethyl ether
  15. customthe extract was dried
  16. customevaporated to dryness

Sources & evidence

ORD record
ord-8b0d2f2f5d5a4b8ab2aed8e6636044d2
Source dataset
uspto-grants-1991_06
Patent number
US05021414

Reaction notes

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