Potassium Hydroxide → HCID 86660365, compound

HRID 713860Notes

Reaction equation

HRID 713860 reaction equation
C([O:3][CH:4]([C:28](=[O:50])[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=[CH:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[C:5](=[O:27])[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=[CH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=O.[OH-].[K+]>CCO>[C:28]([CH:4]([C:5](=[O:27])[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=[CH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[OH:3])(=[O:50])[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=[CH:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 86660366HCID 86660366, compound

Product 1

HCID 86660365HCID 86660365, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The above didocosahexaenoylmethyl formate (III, 1.38 g, 2.1 mmol) and KOH (300 mg) were stirred in 90% EtOH (70 mL) at room temperature under nitrogen for 90 min. Upon completion of the reaction, most of the solvent was evaporated. The resulting mixture was treated with 60 mL of 2M HCl solution. The aqueous phase was extracted with ether (2×75 mL). The combined ether extract was washed with water (2×50 mL), brine (50 mL), and dried over anhydrous MgSO4. Evaporation of the solvent gave 1.18 g of crude IV as yellowish oil. The crude product was purified by column chromatography on silica gel (230-400 mesh, 50 mL) eluted with 0-6% ethyl acetate gradient in hexanes. This gave 1.0 g of didocosahexaenoyl methanol (IV) as colourless oil.

Workup

  1. customUpon completion of the reaction
  2. custommost of the solvent was evaporated
  3. additionThe resulting mixture was treated with 60 mL of 2M HCl solution
  4. extractionThe aqueous phase was extracted with ether (2×75 mL)
  5. extractionThe combined ether extract
  6. washwas washed with water (2×50 mL), brine (50 mL)
  7. dry with materialdried over anhydrous MgSO4
  8. customEvaporation of the solvent

Sources & evidence

ORD record
ord-67f2b4b0ee2042d3b86eec78fcaf7335
Source dataset
uspto-grants-2015_11
Patent number
US09186325B2

Reaction notes

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