Hydrochloric Acid → HCID 21541510, compound

HRID 1076012Notes

Reaction equation

HRID 1076012 reaction equation
[CH2:1]([Al:3](CC)[CH2:4][CH3:5])[CH3:2].[CH:8]#[N:9].[C-]#N.C([Al+]CC)C.[C:17]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]1[C:28](=[O:35])[CH2:29][CH:30]([OH:34])[C:31]=1OC)([O:19][CH3:20])=[O:18].Cl>C1(C)C=CC=CC=1>[C-:8]#[N:9].[CH2:1]([Al+:3][CH2:4][CH3:5])[CH3:2].[C:17]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]1[C:28](=[O:35])[CH2:29][CH:30]([OH:34])[C:31]=1[C:8]#[N:9])([O:19][CH3:20])=[O:18]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 768Hydrogen CyanideHCID 16682930TriethylaluminumHCID 16686413Diethyl aluminum cyanideHCID 21541483HCID 21541483, compound

Product 2

HCID 16686413Diethyl aluminum cyanideHCID 21541510HCID 21541510, compoundYield 76.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

A toluene solution of diethylaluminum cyanide was prepared by reacting 15.7 g of triethylaluminum with 4.1 g of hydrocyanic acid in 300 ml of toluene. Into the obtained toluene solution of diethylaluminium cyanide was added a mixture of 15.4 g of 2-(6'-carbomethoxy-hexyl)-3-methoxy-4-hydroxy-2-cyclopenten-1-one prepared in Step 2 under cooling and the resultant mixture was allowed to stand for 2 hours at room temperature. The reaction mixture was poured into diluted hydrochloric acid under cooling. The organic layer thus formed was separated, and the aqueous layer was extracted with ether. The combined organic layers were washed with aqueous sodium bicarbonate solution and then water and dried over magnesium sulfate. After evaporation of the solvent, the residual oil was purified using chromatography on silica gel to provide 11.6 g of 2-(6'-carbomethoxyhexyl)-3-cyano-4-hydroxy-2-cyclopenten-1-one as an oily material.

Workup

  1. temperatureunder cooling
  2. temperatureunder cooling
  3. customThe organic layer thus formed
  4. customwas separated
  5. extractionthe aqueous layer was extracted with ether
  6. washThe combined organic layers were washed with aqueous sodium bicarbonate solution
  7. dry with materialwater and dried over magnesium sulfate
  8. customAfter evaporation of the solvent
  9. customthe residual oil was purified

Sources & evidence

ORD record
ord-0c778156b88e4b0188dea0dc33ea4a76
Source dataset
uspto-grants-1976_05
Patent number
US03954811

Reaction notes

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