2-(Dimethylamino)ethanol → 2-Dimethylaminoethyl docosahexaenoate

HRID 1859090Notes

Reaction equation

HRID 1859090 reaction equation
[C:1]([OH:24])(=[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:25](N1C=CN=C1)([N:27]1[CH:31]=[CH:30]N=[CH:28]1)=O.CCOC(C)=O.CCCCCC.CN(CCO)C>CC#N.CN(C)C1C=CN=CC=1>[C:1]([O:24][CH2:30][CH2:31][N:27]([CH3:28])[CH3:25])(=[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]

Participants

7

Reactant 4

HCID 79022-(Dimethylamino)ethanolHCID 682631,1'-CarbonyldiimidazoleHCID 175542Docosahexenoic acidHCID 21226206Ethyl acetate hexane

Product 1

HCID 543902942-Dimethylaminoethyl docosahexaenoateYield 92%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of docosahexaenoic acid (0.986 g, 3.0 mmol) in CH3CN (6.0 mL) was added carbonyldiimidazole (0.535 g, 3.3 mmol) in one portion at 0° C. The mixture was allowed to warm to room temperature and stirred at room temperature for 30 min. TLC showed a complete reaction (1:1 EtOAc/hexane). N,N-dimethylaminoethanol (0.89 g, 10.0 mmol) was added dropwise followed by addition of 4-dimethylaminopyridine (0.073 g, 0.60 mmol) The mixture was stirred at room temperature overnight. The solvent was removed by rotary evaporation and the residue was purified on silica gel using 72% EtOAc/hexane, 80% EtOAC/hexane and 100% EtOAc with 0.5% MeOH each to provide the product, 2-dimethylaminoethyl docosahexaenoate (1.098 g, 92%), as a light yellow oil. The product was stored at -20° C. with small amount of β-carotene.

Workup

  1. stirringwas stirred at room temperature overnight
  2. customThe solvent was removed by rotary evaporation
  3. customthe residue was purified on silica gel using 72% EtOAc/hexane, 80% EtOAC/hexane and 100% EtOAc with 0.5% MeOH

Sources & evidence

ORD record
ord-f9811e336ecc44b0ae06c4d5dc38c868
Source dataset
uspto-grants-2000_11
Patent number
US06153653

Reaction notes

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