Diethyl Ether → HCID 86660367, compound

HRID 713861Notes

Reaction equation

HRID 713861 reaction equation
[C:1]([CH:24]([C:26](=[O:48])[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=[CH:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[OH:25])(=[O:23])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=[CH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].C(=O)([O-])[O-].[K+].[K+].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.CCOCC>C(Cl)Cl>[C:26]([C:24]([C:1](=[O:23])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=[CH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[O:25])(=[O:48])[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=[CH:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 86660365HCID 86660365, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 86660367HCID 86660367, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of didocosahexaenoyl methanol (IV, 1.2 g, 1.9 mmol) and anhydrous potassium carbonate (0.1 g) in 30 mL of CH2Cl2 was added pyridinium chlorochromate (PCC, 1.05 g, 4.8 mmol). The resulting suspension was stirred at room temperature for 2 hours. Ether (120 mL) was then added into the mixture, and the resulting brown suspension was filtered through a pad of silica gel (75 mL). The pad was further washed with ether (3×75 mL). The ether filtrate and washes were combined. Evaporation of the solvent gave 1.3 g of an oily residual as a crude product. The crude product was purified by column chromatography on silica gel (230-400 mesh, 40 mL) eluted with 0-3% ethyl acetate in hexanes. This afforded 0.83 g (69%) of didocosahexaenoyl ketone (V).

Workup

  1. filtrationthe resulting brown suspension was filtered through a pad of silica gel (75 mL)
  2. washThe pad was further washed with ether (3×75 mL)
  3. customEvaporation of the solvent

Sources & evidence

ORD record
ord-3d38bef2a0c6454aaf788effc8d22132
Source dataset
uspto-grants-2015_11
Patent number
US09186325B2

Reaction notes

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