Water → HCID 87088126, compound

HRID 1053542Notes

Reaction equation

HRID 1053542 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:26]Br)(=[O:25])[CH2:23][CH3:24].[OH-].[Na+].O.[C:31]1([CH3:37])[CH:36]=CC=C[CH:32]=1>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:1]([O:21][CH:23]([CH3:24])[C:22]([O:26][C:31]([CH3:37])([CH3:36])[CH3:32])=[O:25])[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 5

HCID 962WaterHCID 1140TolueneHCID 14798Sodium HydroxideHCID 11228909Hypobromous acid, anhydride with propanoic acidHCID 59539494HCID 59539494, compound

Product 1

HCID 87088126HCID 87088126, compoundYield 90%

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, (1.00 g, 3.47 mmol), tetrabutylammonium chloride (0.24 g, 0.87 mmol) and t-butyl □-bromo propionate (3.62 g, 17.3 mmol) was dissolved in toluene (36 mL) and placed under nitrogen. An aqueous solution of sodium hydroxide (50%, 8 mL) was added slowly under vigorous stirring and the resulting mixture was stirred at ambient temperature for twenty hours. Water was added and the mixture was 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 2% ethyl acetate in heptane as eluent. Concentration of the appropriate fractions afforded 1.40 g (90% yield) of the title compound as an oil. 1H-NMR (300 MHz, CDCl3): δ 0.95 (t, 3H), 1.41 (d, 3H), 1.48 (s, 9H), 1.48-1.66 (m, 4H), 2.05 (m, 4H), 2.83 (m, 8H), 3.35 (m, 1H), 3.55 (m, 1H), 3.79 (q, 1H), 5.32-5.44 (m, 10H).

Workup

  1. stirringthe resulting mixture was stirred at ambient temperature for twenty hours
  2. extractionthe mixture was extracted three times with ether
  3. extractionThe combined organic extract
  4. washwas washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography on silica gel using 2% ethyl acetate in heptane as eluent

Sources & evidence

ORD record
ord-07caf6a8b2a14f6481c3773f66f89098
Source dataset
uspto-grants-2016_07
Patent number
US09394228B2

Reaction notes

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