Ammonium Chloride → HCID 25008053, compound

HRID 1925672Notes

Reaction equation

HRID 1925672 reaction equation
[C:1](OCC)(=[O:23])/[CH:2]=[CH:3]/[CH:4]=[CH:5]/[CH2:6]/[CH:7]=[CH:8]\[CH2:9]/[CH:10]=[CH:11]\[CH2:12]/[CH:13]=[CH:14]\[CH2:15]/[CH:16]=[CH:17]\[CH2:18]/[CH:19]=[CH:20]\[CH2:21][CH3:22].[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH4+].[Cl-]>C1COCC1>[CH2:1]([OH:23])/[CH:2]=[CH:3]/[CH:4]=[CH:5]/[CH2:6]/[CH:7]=[CH:8]\[CH2:9]/[CH:10]=[CH:11]\[CH2:12]/[CH:13]=[CH:14]\[CH2:15]/[CH:16]=[CH:17]\[CH2:18]/[CH:19]=[CH:20]\[CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 57668524HCID 57668524, compound

Product 1

HCID 25008053HCID 25008053, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Ethyl (2E,4E,7Z,10Z,13Z,16Z,19Z)-docosa-2,4,7,10,13,16,19-heptaenoate (14) (0.12 g, 0.34 mmol) was dissolved in dry THF (3 mL) and added dropwise to a stirred suspension of LAH (0.013 g, 0.35 mmol) in dry THF (7 mL) at 0° C. The mixture was stirred at 0° C. for 45 minutes, added saturated NH4Cl (5 mL) and filtered through a short pad of celite. The celite was washed with water (10 mL) and heptane (10 mL) and the combined aqueous layer was extracted with heptane (10 mL). The combined organic layer was dried (MgSO4) and purified by flash chromatography (heptane:EtOAc 7:1). This afforded 0.070 g (66%) of the title compound 16 as colourless oil.

Workup

  1. filtrationfiltered through a short pad of celite
  2. washThe celite was washed with water (10 mL) and heptane (10 mL)
  3. extractionthe combined aqueous layer was extracted with heptane (10 mL)
  4. dry with materialThe combined organic layer was dried (MgSO4)
  5. custompurified by flash chromatography (heptane:EtOAc 7:1)

Sources & evidence

ORD record
ord-fd081aa7ceb04268ac6d9c816e325ee0
Source dataset
uspto-grants-2012_05
Patent number
US08178708B2

Reaction notes

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