Water → HCID 86665236, compound

HRID 1053544Notes

Reaction equation

HRID 1053544 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].[C:22]([O:27]Br)(=[O:26])[CH:23]([CH3:25])[CH3:24].[OH-].[Na+].O>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH2:1]([O:21][C:23]([CH3:25])([CH3:24])[C:22]([O:27][C:23]([CH3:25])([CH3:24])[CH3:22])=[O:26])[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

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21270289HCID 21270289, compoundHCID 59539494HCID 59539494, compound

Product 1

HCID 86665236HCID 86665236, compoundYield 44.4%

Reagents, catalysts & solvents 2

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 1140TolueneSolvent

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 □-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-7a41632dda4040be81151dc73bdba513
Source dataset
uspto-grants-2016_07
Patent number
US09394228B2

Reaction notes

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