Trifluoroacetic acid → HCID 58264329, compound

HRID 1473833Notes

Reaction equation

HRID 1473833 reaction equation
[CH2:1]([O:19][CH2:20][CH:21]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]/[CH:36]=[CH:37]\[CH2:38]/[CH:39]=[CH:40]\[CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[CH2:22][O:23]CC=C)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].FC(F)(F)C(O)=O>C(O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:1]([O:19][CH2:20][CH:21]([CH2:22][OH:23])[O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]/[CH:36]=[CH:37]\[CH2:38]/[CH:39]=[CH:40]\[CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58264321HCID 58264321, compound

Product 1

HCID 58264329HCID 58264329, compoundYield 65.4%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolvent

Procedure

1,2-Dilinoleyloxy-3-allyloxypropane (25) (18 g, 28.6 mmol) was dissolved in ethanol (150 mL) in a 500 mL round bottom flask with a stir bar. Trifluoroacetic acid (15 mL) and tetrakis (triphenylphosphine) palladium(0) (5.0 g, 4.3 mmol) were added and the flask flushed with nitrogen. A water condenser was fitted and the flask wrapped tin foil to reduce exposure to light. The reaction was refluxed under nitrogen overnight. The solution was concentrated to an orange oil, then redissolved in DCM (250 mL), and washed with water (2×200 mL) and saturated brine (1×200 mL). The aqueous phases were combined and extracted with DCM (2×100 mL). Organic phases were combined, dried over MgSO4 and concentrated. The crude product was purified by column chromatography to yield 1,2-dilinoleylglycerol as a colorless oil (11.0 g, 18.7 mmol, 65.3%).

Workup

  1. customthe flask flushed with nitrogen
  2. customA water condenser was fitted
  3. temperatureThe reaction was refluxed under nitrogen overnight
  4. concentrationThe solution was concentrated to an orange oil
  5. dissolutionredissolved in DCM (250 mL)
  6. washwashed with water (2×200 mL) and saturated brine (1×200 mL)
  7. extractionextracted with DCM (2×100 mL)
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated
  10. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-f8782d0ee93b42f8a9e293785338a986
Source dataset
uspto-grants-2015_04
Patent number
US09018187B2

Reaction notes

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