HCID 20062275, compound → HCID 178458853, compound

HRID 1084668Notes

Reaction equation

HRID 1084668 reaction equation
[OH:1][C:2]1[CH:7](C(OCC)=O)[CH:6]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19]C(=O)CC)[CH:14]=2)[CH2:5][C:4](=[O:24])[C:3]=1[C:25](=[O:28])[CH2:26][CH3:27].CO.C(Cl)(Cl)Cl>[OH-].[Na+]>[C:25]([C:3]1[C:4](=[O:24])[CH2:5][CH:6]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[CH:14]=2)[CH2:7][C:2]=1[OH:1])(=[O:28])[CH2:26][CH3:27]

Participants

4

Reactant 2

HCID 20062275HCID 20062275, compoundHCID 21584188Chloroform methanol

Product 1

HCID 178458853HCID 178458853, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 36.0 g (0.0927 mol) of 3-hydroxy-5-(3-propionyloxyphenyl)-2-propionyl-4-(carboethoxy)-cyclohex-2-en-1-one in 520 mL of 1N NaOH was heated at 75° C. for 4 hours and cooled to room temperature. The reaction mixture was filtered and the filtrate was diluted with 100 mL of water and acidified with 50 mL of concentrated HCl with the product precipitating as an oil. The oil was dissolved in a mixture of 300 mL of methylene chloride and 200 mL of ethyl ether. The organic layer was separated, washed twice with 200 mL portions of water and dried over Na2SO4. The solvent was removed in vacuo leaving 20.4 g of a partially crystalline product which was purified by column chromatography using a 20:80 acetone:chloroform mixture as eluent. The fractions containing the product were combined and the solvent removed in vacuo leaving 13.1 g (54.4 percent of theoretical) of the above named product which melted at 124°-131° C.; Rf -0.38 (silica gel, 10:90 methanol-chloroform), 1H NMR (CDCl3 +D6 -DMSO): δ1.10 (t, 3H, --CH2CH3), 2.5-3.5 (m, 7H, ring protons and --CH2CH3), 6.55-7.25 (m, 3H, ArH), 8.8 5 (s, H, ArOH), 18.1 (s, 1H, OH).

Workup

  1. filtrationThe reaction mixture was filtered
  2. additionthe filtrate was diluted with 100 mL of water
  3. customprecipitating as an oil
  4. dissolutionThe oil was dissolved in a mixture of 300 mL of methylene chloride and 200 mL of ethyl ether
  5. customThe organic layer was separated
  6. washwashed twice with 200 mL portions of water
  7. dry with materialdried over Na2SO4
  8. customThe solvent was removed in vacuo
  9. customleaving 20.4 g of a partially crystalline product which
  10. customwas purified by column chromatography
  11. additionThe fractions containing the product
  12. customthe solvent removed in vacuo
  13. customleaving 13.1 g (54.4 percent of theoretical) of the

Sources & evidence

ORD record
ord-6f3c56d6e8ac4db9bab534cc941b37c2
Source dataset
uspto-grants-1991_04
Patent number
US05006159

Reaction notes

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