Diethyl Ether → HCID 86665234, compound

HRID 1028079Notes

Reaction equation

HRID 1028079 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([O:28][CH:29]([CH3:33])[C:30]([O-:32])=[O:31])[CH2:9][CH2:10][CH2:11]/[CH:12]=[CH:13]\[CH2:14]/[CH:15]=[CH:16]\[CH2:17]/[CH:18]=[CH:19]\[CH2:20]/[CH:21]=[CH:22]\[CH2:23]/[CH:24]=[CH:25]\[CH2:26][CH3:27].C(OCC)C>ClCCl.CCCCCCC>[CH2:8]([O:28][CH:29]([CH3:33])[C:30]([OH:32])=[O:31])[CH2:9][CH2:10][CH2:11]/[CH:12]=[CH:13]\[CH2:14]/[CH:15]=[CH:16]\[CH2:17]/[CH:18]=[CH:19]\[CH2:20]/[CH:21]=[CH:22]\[CH2:23]/[CH:24]=[CH:25]\[CH2:26][CH3:27]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 6422Trifluoroacetic acidHCID 86665235HCID 86665235, compound

Product 1

HCID 86665234HCID 86665234, compoundYield 41.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8900HeptaneSolvent

Procedure

Trifluoroacetic acid (2 mL) was added to a solution of 2-((5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenyloxy)propanoate (1.40 g, 3.36 mmol) in dichloromethane (10 mL) held under nitrogen and the reaction mixture was stirred at room temperature for three hours. Diethyl ether (50 mL) was added and the organic phase was washed with water (30 mL), dried (Na2SO4) and concentrated. The residue was subjected to flash chromatography on silica gel using increasingly polar mixtures of heptane, ethyl acetate and formic acid (95:5:0.25→80:20:1) as eluent. Concentration of the appropriate fractions afforded 0.67 g of slightly impure product. This material was dissolved in heptane (15 mL), washed three times with water (5 mL), dried (Na2SO4), filtered and concentrated to afford 0.50 g (41% yield) of the title compound as an oil. 1H-NMR (300 MHz, CDCl3): δ 0.99 (t, 3H), 1.40-1.48 (m, 5H), 1.67 (m, 2H), 2.09 (m, 4H), 2.80-2.60 (m, 8H), 3.53 (m, 2H), 4.01 (q, 1H), 5.31-5.47 (m, 10H); MS (electro spray): 359.2 [M−H]−.

Workup

  1. washthe organic phase was washed with water (30 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. temperatureincreasingly polar mixtures of heptane, ethyl acetate and formic acid (95:5:0.25→80:20:1) as eluent
  5. customConcentration of the appropriate fractions afforded 0.67 g of slightly impure product
  6. washwashed three times with water (5 mL)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-b2b524ccc2eb4b1ebf3f500b739252de
Source dataset
uspto-grants-2014_05
Patent number
US08735436B2

Reaction notes

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