Bromide ion → (6Z,9Z,28E,31E)-heptatriaconta-6,9,28,31-tetraen-19-ol

HRID 537832Notes

Reaction equation

HRID 537832 reaction equation
[Mg].[Br-].II.[CH:5](=[O:24])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]/[CH:14]=[CH:15]\[CH2:16]/[CH:17]=[CH:18]\[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].Cl>C1COCC1.O>[CH3:23][CH2:22][CH2:21][CH2:20][CH2:19]/[CH:18]=[CH:17]\[CH2:16]/[CH:15]=[CH:14]\[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH:5]([OH:24])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]/[CH:13]=[CH:14]/[CH2:15]/[CH:16]=[CH:17]/[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

8

Reactant 5

HCID 259Bromide ionHCID 313Hydrochloric AcidHCID 807IodineHCID 5462224Magnesium2×HCID 57500215(10Z,13Z)-nonadeca-10,13-dienal

Product 1

HCID 86684839(6Z,9Z,28E,31E)-heptatriaconta-6,9,28,31-tetraen-19-olYield 139.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

A 100 mL round bottom flask, charged with magnesium turnings (355 mg, 14.6 mmol) and a stir bar, was dried with a high temperature heat gun for 5 minutes. Upon cooling under nitrogen, THF (6 mL) was added followed by linolaidyl bromide (6.02 g, 18.3 mmol). The mixture was heated to 45° C. and a single grain of iodine was added. The reaction was refluxed for 2.5 hours then cooled to room temperature where upon a solution of (10Z,13Z)-nonadeca-10,13-dienal (3.4 g, 12.4 mmol) in THF (10 mL) was added. The solution was stirred for 1.5 hours at room temperature then poured into water (150 mL) and 5% HCl (50 mL) was added. Upon dissolution of the magnesium, the solution was extracted with ether (2×150 mL). The combined ether extracts were dried on magnesium sulfate, filtered and concentrated in vacuo to dryness. The residue was purified by column chromatography (100% hexanes) to afford the title compound as a colorless oil (4.57 g, 71%).

Workup

  1. customwas dried with a high temperature
  2. temperatureheat gun for 5 minutes
  3. temperatureUpon cooling under nitrogen
  4. additionTHF (6 mL) was added
  5. temperatureThe reaction was refluxed for 2.5 hours
  6. additionwas added
  7. additionwas added
  8. extractionthe solution was extracted with ether (2×150 mL)
  9. dry with materialThe combined ether extracts were dried on magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo to dryness
  12. customThe residue was purified by column chromatography (100% hexanes)

Sources & evidence

ORD record
ord-191b2e4b1fd144799da10cf414f0f371
Source dataset
uspto-grants-2014_10
Patent number
US08865675B2

Reaction notes

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