Hydrochloric Acid → HCID 58381713, compound

HRID 410043Notes

Reaction equation

HRID 410043 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C(=O)([S:9][CH2:10][CH2:11]/[CH:12]=[CH:13]\[CH2:14]/[CH:15]=[CH:16]\[CH2:17]/[CH:18]=[CH:19]\[CH2:20]/[CH:21]=[CH:22]\[CH2:23][CH3:24])C.Cl>C(OCC)C>[CH2:10]([SH:9])[CH2:11]/[CH:12]=[CH:13]\[CH2:14]/[CH:15]=[CH:16]\[CH2:17]/[CH:18]=[CH:19]\[CH2:20]/[CH:21]=[CH:22]\[CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 58381707HCID 58381707, compound

Product 1

HCID 58381713HCID 58381713, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

LiAlH4 (2.05 g, 54.1 mmol) was suspended in dry diethyl ether (100 mL) at 0° C. under inert atmosphere. To this suspension was added dropwise a solution of S-(3Z,6Z,9Z,12Z)-pentadeca-3,6,9,12-tetraenyl ethanethioate (13.7 g, 49.2 mmol) in dry diethyl ether (50 mL) and the resulting grey mixture was stirred at 0° C. for ten minutes and then at ambient temperature for 30 minutes. The mixture was cooled to ˜5° C., added 1M HCl until pH=2 and filtrated through a short pad of celite. The pad was washed with water and diethyl ether, the phases were separated and the aqueous phase was extracted twice with diethyl ether (100 mL each). The combined organic extracts were dried (Na2SO4), filtered and concentrated under reduced pressure to afford 7.8 g (67% yield) of the title compound as oil.

Workup

  1. temperatureThe mixture was cooled to ˜5° C.
  2. filtrationfiltrated through a short pad of celite
  3. washThe pad was washed with water and diethyl ether
  4. customthe phases were separated
  5. extractionthe aqueous phase was extracted twice with diethyl ether (100 mL each)
  6. dry with materialThe combined organic extracts were dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3f2f6110b10c4292aee634579015c33f
Source dataset
uspto-grants-2014_06
Patent number
US08759558B2

Reaction notes

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