Water → HCID 49787413, compound

HRID 1028081Notes

Reaction equation

HRID 1028081 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([O:28][C:29]([CH3:38])([CH3:37])[C:30]([O:32]C(C)(C)C)=[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].O>ClCCl.CCCCCCC>[CH2:8]([O:28][C:29]([CH3:37])([CH3:38])[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 962WaterHCID 6422Trifluoroacetic acidHCID 86665236HCID 86665236, compound

Product 1

HCID 49787413HCID 49787413, compoundYield 8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8900HeptaneSolvent

Procedure

Trifluoroacetic acid (5 mL) was added to a solution of tert-butyl 2-((5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenyloxy)-2-methylpropanoate (600 mg, 1.39 mmol) in dichloromethane (20 mL) under nitrogen and the reaction mixture was stirred at room temperature for two hours. Water was added and the aqueous phase was extracted twice with dichloromethane. The combined organic extract was washed with brine, dried (Na2SO4), filtered and concentrated. The residue was purified by flash chromatography on silica gel using a mixture of heptane, ethyl acetate and formic acid (80:20:1) as eluent. The appropriate fractions were concentrated and the residue (135 mg) was purified further by flash chromatography on silica gel using a gradient of 5-10% of a mixture of ethyl acetate and formic acid (95:5) in heptane as eluent. Concentration of the appropriate fractions afforded 80 mg slightly impure product. This material was dissolved in heptane (5 mL), washed twice with water (5 mL), dried (Na2SO4), filtered and concentrated to afford 40 mg (8% yield) of the title compound as an oil. 1H-NMR (300 MHz, CDCl3): δ 0.99 (t, 3H), 1.47 (s, 6H), 1.64 (m, 2H), 2.07 (m, 4H), 2.81-2.88 (m, 8H), 3.46 (t, 2H), 5.29-5.44 (m, 10H); MS (electro spray): 373.3 [M−H]−

Workup

  1. extractionthe aqueous phase was extracted twice with dichloromethane
  2. extractionThe combined organic extract
  3. washwas washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography on silica gel using
  8. additiona mixture of heptane, ethyl acetate and formic acid (80:20:1) as eluent
  9. concentrationThe appropriate fractions were concentrated
  10. customthe residue (135 mg) was purified further by flash chromatography on silica gel using a gradient of 5-10% of a mixture of ethyl acetate and formic acid (95:5) in heptane as eluent
  11. customConcentration of the appropriate fractions afforded 80 mg slightly impure product
  12. washwashed twice with water (5 mL)
  13. dry with materialdried (Na2SO4)
  14. filtrationfiltered
  15. concentrationconcentrated

Sources & evidence

ORD record
ord-5486a0c3e1a94b8bb929a3f852704e08
Source dataset
uspto-grants-2014_05
Patent number
US08735436B2

Reaction notes

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