Hydrochloric Acid → HCID 58381688, compound

HRID 410050Notes

Reaction equation

HRID 410050 reaction equation
[CH2:1]([S:16]([CH:19]([CH2:25][CH3:26])[C:20]([O:22]CC)=[O:21])(=[O:18])=[O:17])[CH2:2]/[CH:3]=[CH:4]\[CH2:5]/[CH:6]=[CH:7]\[CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH3:15].[Li+].[OH-].O.Cl>C(O)C>[CH2:1]([S:16]([CH:19]([CH2:25][CH3:26])[C:20]([OH:22])=[O:21])(=[O:17])=[O:18])[CH2:2]/[CH:3]=[CH:4]\[CH2:5]/[CH:6]=[CH:7]\[CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH3:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 58381725HCID 58381725, compound

Product 1

HCID 58381688HCID 58381688, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

Ethyl 2-((3Z,6Z,9Z,12Z)-pentadeca-3,6,9,12-tetraenylsulfonyl)butanoate (370 mg, 0.97 mmol) was dissolved in ethanol (10 mL) and added a solution of LiOH in H2O (1 M, 3.9 mL, 3.9 mmol). The resulting mixture was stirred at 60° C. for three hours, cooled, added 0.1 M HCl until pH=2 and extracted twice with diethyl ether (15 mL each). The combined organic layer was washed with brine (15 mL), dried, filtrated, concentrated in vacuo and purified by flash chromatography on silica gel (heptane:EtOAc w/5% HCOOH 4:1). Concentration of the appropriate fractions afforded 250 mg (73% yield) of the title compound as an oil.

Workup

  1. temperaturecooled
  2. extractionextracted twice with diethyl ether (15 mL each)
  3. washThe combined organic layer was washed with brine (15 mL)
  4. customdried
  5. filtrationfiltrated
  6. concentrationconcentrated in vacuo
  7. custompurified by flash chromatography on silica gel (heptane:EtOAc w/5% HCOOH 4:1)

Sources & evidence

ORD record
ord-2f6635ac00524558bdac910a878c58c7
Source dataset
uspto-grants-2014_06
Patent number
US08759558B2

Reaction notes

Loading…