Hydrochloric Acid → HCID 70402744, compound

HRID 1789613Notes

Reaction equation

HRID 1789613 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][C:2]1[C:3](=[O:25])[C:4](=[CH:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])[C@@H:5]([CH:7]=[CH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 56633877HCID 56633877, compound

Product 1

HCID 70402744HCID 70402744, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

16 mg (46 microliters) of (4R)-2,3-epoxy-4-(1-octenyl)-5-(6-methoxylcarbonylhexylidene)cyclopentenone was dissolved in 1 ml of acetone. To the solution was added 0.1 ml of concentrated hydrochloric acid, and then the mixture was stirred for 30 minutes. A saturated aqueous solution of sodium hydrogencarbonate was added, and the mixture 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 concentrated and subjected to silica gel column chromatography (silica gel, 5 g; eluent, hexane:ethyl acetate=15:1→6:1) to give 11 mg (yield 65%) of (4S)-2-chloro-4-(1-octenyl)-5-(6-methoxycarbonylhexylidene)-2-cyclopentenone.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationThe dried product was concentrated

Sources & evidence

ORD record
ord-253b657113ad46e7a6369acb204fc5d8
Source dataset
uspto-grants-1987_08
Patent number
US04689426

Reaction notes

Loading…