Hydrochloric Acid → HCID 56620186, compound

HRID 1789610Notes

Reaction equation

HRID 1789610 reaction equation
P([O-])([O-])([O-])=O.[Cl:6][C:7]1[C:8](=[O:26])[C:9](=[CH:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([O:24]C)=[O:23])[CH:10]([CH2:12][CH2:13][CH2:14][CH3:15])[CH:11]=1.Cl.S([O-])([O-])(=O)=O.[NH4+].[NH4+]>CC(C)=O>[Cl:6][C:7]1[C:8](=[O:26])[C:9](=[CH:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23])[CH:10]([CH2:12][CH2:13][CH2:14][CH3:15])[CH:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1061PhosphateHCID 6097028Ammonium SulfateHCID 56622655HCID 56622655, compound

Product 1

HCID 56620186HCID 56620186, compoundYield 39.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
30 °C

Procedure

20 ml of phosphate buffer (pH8) was added to a solution of 200 mg (0.64 mmol) of 2-chloro-4-butyl-5-(6-methoxycarbonylhexylidene)-2-cyclopentenone in 15 ml of acetone, and then 0.4 ml of an aqueous solution of pig liver esterase was added. The mixture was stirred at 30° C. for 60 hours. 1N hydrochloric acid was added to the reaction mixture to adjust the pH to 4, and then the mixture was saturated with ammonium sulfate. It was filtered, and then extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. The dried product was filtered, concentrated and subjected to silica gel column chromatography (silica gel, 10 g; eluent, hexane:ethyl acetate=3.2) to give 75 mg (yield 39%) of 2-chloro-4-butyl-5-(6-carboxyhexylidene)-2-cyclopentenone.

Workup

  1. filtrationIt was filtered
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe dried product was filtered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-66849e19f2dd45bda6a5b16a7d070d63
Source dataset
uspto-grants-1987_08
Patent number
US04689426

Reaction notes

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