Hydrochloric Acid → HCID 54246591, compound

HRID 1789615Notes

Reaction equation

HRID 1789615 reaction equation
O1[C:6]2[C@@H:5]([CH:7]=[CH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[C:4](=[CH:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])[C:3](=[O:25])[C:2]1=2.[ClH:26].C(=O)([O-])O.[Na+]>CC(C)=O>[Cl:26][CH:2]1[CH2:6][C@H:5]([CH:7]=[CH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[C:4](=[CH:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])[C:3]1=[O:25]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 56614884HCID 56614884, compound

Product 1

HCID 54246591HCID 54246591, compoundYield 4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 450 mg (1.29 mmol) of (4S)-2,3-epoxy-4-(1-octenyl)-5-(6-methoxycarbonylhexylidene)cyclopentenone in 12 ml of acetone was added 2 ml of concentrated hydrochloric acid at room temperature under stirring. The mixture was stirred for 2 hours. A saturated aqueous solution of sodium hydrogencarbonate was added, and the mixture was concentrated. The product was 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, 40 g; eluent, hexane:ethyl acetate=10:1→5:1) to give 19 mg (yield 4%) of a less polar isomer (Z-form) of (4R)-2-chloro-4-(1-octenyl)-5-(6-methoxycarbonylhexylidene)cyclopentanone and 177 mg (yield 37%) of a more polar isomer (E-form).

Workup

  1. stirringThe mixture was stirred for 2 hours
  2. concentrationthe mixture was concentrated
  3. extractionThe product was extracted with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationThe dried product was filtered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-81a9a4d8c7904d059454a7d52ad6da26
Source dataset
uspto-grants-1987_08
Patent number
US04689426

Reaction notes

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