Hydrochloric Acid → HCID 56622655, compound

HRID 1789609Notes

Reaction equation

HRID 1789609 reaction equation
O1[C:6]2[CH:5]([CH2:7][CH2:8][CH2:9][CH3:10])[C:4](=[CH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])[C:3](=[O:21])[C:2]1=2.[ClH:22].C(=O)([O-])O.[Na+]>CC(C)=O>[Cl:22][C:2]1[C:3](=[O:21])[C:4](=[CH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH:5]([CH2:7][CH2:8][CH2:9][CH3:10])[CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 56621154HCID 56621154, compound

Product 1

HCID 56622655HCID 56622655, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

300 mg (1.02 mmol) of 2,3-epoxy-4-butyl-5-(6-methoxycarbonylhexylidene)cyclopentenone was dissolved in 3 ml of acetone. 0.5 ml of concentrated hydrochloric acid was added to the solution and the mixture was stirred for 50 minutes. A saturated aqueous solution of sodium hydrogen carbonate was added thereto and was extracted with hexane. The organic layer was washed with a saturated saline solution, dried over sodium sulfate anhydride, filtrated, and subjected to column chromatography on silica gel (silica gel, 20 g; eluent, cyclohexane:ethyl acetate=10:1) to obtain 28 mg (yield 9%) of a less polar isomer (Z-form) of 2-chloro-4-butyl-5-(6-methoxycarbonyl-hexylidene)-2-cyclopentenone and 183 mg (yield 57%) of its more polar isomer (E-form).

Workup

  1. extractionwas extracted with hexane
  2. washThe organic layer was washed with a saturated saline solution
  3. dry with materialdried over sodium sulfate anhydride
  4. filtrationfiltrated

Sources & evidence

ORD record
ord-5a9561b519a84b979202aaeaf20d37af
Source dataset
uspto-grants-1987_08
Patent number
US04689426

Reaction notes

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