Water → HCID 86665236, compound

HRID 1028080Notes

Reaction equation

HRID 1028080 reaction equation
[CH2:1]([OH:21])[CH2:2][CH2:3][CH2:4]/[CH:5]=[CH:6]\[CH2:7]/[CH:8]=[CH:9]\[CH2:10]/[CH:11]=[CH:12]\[CH2:13]/[CH:14]=[CH:15]\[CH2:16]/[CH:17]=[CH:18]\[CH2:19][CH3:20].[OH-:22].[Na+].[OH2:24].[C:25]1([CH3:31])[CH:30]=CC=C[CH:26]=1>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:1]([O:21][C:25]([CH3:26])([CH3:31])[C:30]([O:24][C:25]([CH3:31])([CH3:30])[CH3:26])=[O:22])[CH2:2][CH2:3][CH2:4]/[CH:5]=[CH:6]\[CH2:7]/[CH:8]=[CH:9]\[CH2:10]/[CH:11]=[CH:12]\[CH2:13]/[CH:14]=[CH:15]\[CH2:16]/[CH:17]=[CH:18]\[CH2:19][CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 14798Sodium HydroxideHCID 59539494HCID 59539494, compound

Product 1

HCID 86665236HCID 86665236, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 70681Tetrabutylammonium ChlorideCatalyst

Procedure

A mixture of (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaen-1-ol, (0.83 g, 3.14 mmol), tetrabutylammonium chloride (0.24 g, 0.85 mmol) and t-butyl α-bromo isobutyrate (3.50 g, 15.7 mmol) was dissolved in toluene (15 mL) and placed under nitrogen. An aqueous solution of sodium hydroxide (50%, 5 mL) was added slowly under vigorous stirring at room temperature. The resulting mixture was heated to 60° C. and stirred for six hours. The mixture was cooled, added water and extracted three times with ether. The combined organic extract was washed with brine, dried (Na2SO4), filtered and concentrated. The residue was purified by flash chromatography on silica gel using a gradient of 5-10% ethyl acetate in heptane as eluent. Concentration of the appropriate fractions afforded 0.60 g (44% yield) of the title compound as an oil. MS (electro spray): 453.3 [M+Na]+.

Workup

  1. temperatureThe resulting mixture was heated to 60° C.
  2. stirringstirred for six hours
  3. temperatureThe mixture was cooled
  4. extractionextracted three times with ether
  5. extractionThe combined organic extract
  6. washwas washed with brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified by flash chromatography on silica gel using a gradient of 5-10% ethyl acetate in heptane as eluent

Sources & evidence

ORD record
ord-2536c05290894130931798c4ec299952
Source dataset
uspto-grants-2014_05
Patent number
US08735436B2

Reaction notes

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