Dichloromethane → Methyl 8-[2-[(2-pentylcyclopropyl)methyl]cyclopropyl]octanoate

HRID 2376793Notes

Reaction equation

HRID 2376793 reaction equation
[CH3:1][O:2][C:3](=[O:21])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]/[CH:11]=[CH:12]\[CH2:13]/[CH:14]=[CH:15]\[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].ClCCl.C([Zn][CH2:28][CH3:29])C>CCCCCC>[CH3:1][O:2][C:3](=[O:21])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]1[CH2:12][CH:13]1[CH2:14][CH:15]1[CH2:16][CH:17]1[CH2:18][CH2:19][CH2:20][CH2:28][CH3:29]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 5284421Methyl linoleateHCID 178418750HCID 178418750, compound

Product 1

HCID 534623Methyl 8-[2-[(2-pentylcyclopropyl)methyl]cyclopropyl]octanoate

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a mixture of linoleic acid methyl ester (2.5 g) and dichloromethane (50 ml), a 0.99M solution of diethylzinc (103 ml) in n-hexane was added under a nitrogen atmosphere. The mixture was cooled in an ice-water bath (−5° C. to 0° C.) and stirred for 1 hour at this temperature. Diodomethane (16.4 ml) was added to the mixture, and the mixture was stirred at ambient temperature overnight. After evaporation in vacuo of the solvent, the reacting mixture was dissolved in a mixture of ethyl acetate (EA) and a saturated aqueous solution of ammonium chloride. The separated organic layer was washed with water and dried over magnesium sulfate. After filtration, the filtrate was concentrated in vacuo. The obtained residue was purified by chromatography on silica gel (eluted with 1% EA in n-hexane). The fractions including 8-(2-((2-pentyl-cyclopropan-1-yl)methyl)cyclopropyl)octanoic acid methyl ester were collected and concentrated in vacuo to give 8-(2-((2-pentylcyclopropan-1-yl)methyl)cyclopropyl)octanoic acid methyl ester (2.81 g) as an oil.

Workup

  1. temperatureThe mixture was cooled in an ice-water bath (−5° C. to 0° C.)
  2. additionDiodomethane (16.4 ml) was added to the mixture
  3. stirringthe mixture was stirred at ambient temperature overnight
  4. customAfter evaporation in vacuo of the solvent
  5. dissolutionthe reacting mixture was dissolved in a mixture of ethyl acetate (EA)
  6. washThe separated organic layer was washed with water
  7. dry with materialdried over magnesium sulfate
  8. filtrationAfter filtration
  9. concentrationthe filtrate was concentrated in vacuo
  10. customThe obtained residue was purified by chromatography on silica gel (eluted with 1% EA in n-hexane)
  11. customwere collected
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-54168a1698f04d9b8a3def363194c0c4
Source dataset
uspto-grants-2008_12
Patent number
US07468389B2

Reaction notes

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