1-Iodooctadecane → HCID 86741269, compound

HRID 235706

Reaction equation

HRID 235706 reaction equation
C(NC1CCCCC1)(C)C.C([Li])CCC.[CH2:16]1[O:28][C:19]([CH3:27])([CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[O:18][CH2:17]1.[CH2:29](I)[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46]>O1CCCC1.CS(C)=O>[CH3:27][C:19]1([CH2:20][CH:21]([CH2:46][CH2:45][CH2:44][CH2:43][CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH3:29])[C:22]([O:24][CH2:25][CH3:26])=[O:23])[O:18][CH2:17][CH2:16][O:28]1

Participants

7

Reactant 4

HCID 124021-IodooctadecaneHCID 62386CyclohexylisopropylamineHCID 70332Ethyl 2-methyl-1,3-dioxolane-2-propionateHCID 178418339Butyllithium

Product 1

HCID 86741269HCID 86741269, compoundYield 52.5%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-70 °C

Procedure

To a solution of about 34.35 g of isopropylcyclohexylamine in about 150 ml of tetrahydrofuran at about -20° C. was added about 156.89 ml of an about 1.55M n-butyllithium, at a rate so that the final temperature reached about 10° C. The solution was then cooled to about -70° C. and about 25 g of ethyl levulinate ethylene ketal was added dropwise. After about 15 minutes, the solution was warmed to about -30° C. and maintained at that temperature while it was added rapidly, dropwise to a stirred solution of about 80.44 g of octadecyl iodide in about 150 ml of dimethyl sulfoxide and about 50 ml of tetrahydrofuran at room temperature. This mixture was stirred overnight, the volatile solvents were removed and water was added. The resulting solid was collected by filtration and extracted with ether giving a solution and a solid. This solution and original filtrate were combined and extracted with ether. This ether extract was dried and the solvent removed giving an oil. This oil was subjected to HPLC, eluting with hexane:ether (about 9:1). The product band was collected and the solvent removed, giving about 30.76 g of the desired title compound as a solid, mp 33°-34° C.

Workup

  1. customreached about 10° C
  2. temperaturethe solution was warmed to about -30° C.
  3. temperaturemaintained at that temperature while it
  4. customthe volatile solvents were removed
  5. additionwater was added
  6. filtrationThe resulting solid was collected by filtration
  7. extractionextracted with ether giving a solution
  8. extractionextracted with ether
  9. extractionThis ether extract
  10. customwas dried
  11. customthe solvent removed
  12. customgiving an oil
  13. washeluting with hexane
  14. customThe product band was collected
  15. customthe solvent removed

Sources & evidence

ORD record
ord-cd2d535607a443efadadb986a5a6e792
Source dataset
uspto-grants-1987_02
Patent number
US04640913

Linked notes

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