Hydrochloric Acid → HCID 14232973, compound

HRID 580668Notes

Reaction equation

HRID 580668 reaction equation
[CH2:1]([C:5]1([CH:36]2[CH2:40][CH2:39][CH2:38][CH2:37]2)[CH2:13][C:12]2[C:7](=[C:8]([Cl:34])[C:9]([Cl:33])=[C:10]([C:14](C(OCC)=O)([CH2:20][CH2:21][CH2:22][C:23]([O:25]CC)=[O:24])[C:15]([O:17]CC)=[O:16])[CH:11]=2)[C:6]1=[O:35])[CH2:2][CH2:3][CH3:4].[OH-].[Na+].Cl>CO.O>[CH2:1]([C:5]1([CH:36]2[CH2:37][CH2:38][CH2:39][CH2:40]2)[CH2:13][C:12]2[C:7](=[C:8]([Cl:34])[C:9]([Cl:33])=[C:10]([CH:14]([CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])[C:15]([OH:17])=[O:16])[CH:11]=2)[C:6]1=[O:35])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 14232972HCID 14232972, compound

Product 1

HCID 14232973HCID 14232973, compoundYield 84.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

The diethyl 2-(2-butyl-6,7-dichloro-2-cyclopentyl-2,3-dihyro-1-oxo-1H-inden-5-yl)-2-(ethoxycarbonyl)-1,6-hexanedioate (6.5 g) was refluxed with sodium hydroxide (5 g) dissolved in methanol (100 ml) and water (20 ml) for 3 hours. The mixture was cooled, diluted with water, acidified with hydrochloric acid and extracted with diethyl ether. The organic extracts were washed with water, dried over MgSO4 and concentrated to obtain 2-(2-butyl-6,7-dichloro-2-cyclopentyl-2,3-dihydro-1-oxo-1H-inden-5-yl)-1,6-hexanedioic acid (4.3 g). The dioic acid was heated at 130°-135° C. for 25 minutes with copper powder (1.52 g) in quinoline (35 ml). The mixture was cooled, poured into water and extracted with diethyl ether after acidification with hydrochloric acid. The organic extracts were washed with water, dried over MgSO4 and concentrated under vacuum. The residue was chromatographed twice on silica eluting with a mixture of toluene, dioxane and acetic acid in the ratio of 900:80:10 to obtain 2.9 g of the product as viscous oil.

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with diethyl ether
  3. washThe organic extracts were washed with water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2cc8dfcd54bc4a3bbbac83c9dd7f0e8a
Source dataset
uspto-grants-1988_06
Patent number
US04754061

Reaction notes

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