Hydrochloric Acid → HCID 58681650, compound

HRID 1583253Notes

Reaction equation

HRID 1583253 reaction equation
[C:1]([O:20][CH3:21])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[CH:22]([N-]C1CCCCC1)(C)C.[Li+].CI.Cl>O1CCCC1>[CH3:22][CH:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:1]([O:20][CH3:21])=[O:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 5364509Methyl OleateHCID 10877271Lithium cyclohexylisopropylamide

Product 1

HCID 58681650HCID 58681650, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of methyl oleoate (0.054 mole) in tetrahydrofuran (100 ml) was added dropwise to a freshly prepared cold solution of lithium isopropyl cyclohexyl amide (1.2 eq.) in tetrahydrofuran (400 ml) over 4.75 hrs. Methyl iodide (1.5 eq.) was added dropwise rapidly and the reaction was allowed to come to room temperature. The reaction was stripped of solvent to give an orange oil. The material was added to 1N hydrochloric acid (100 ml) and extracted into ethyl ether. The ethyl ether was washed with water (100 ml), dried over sodium sulfate, filtered and stripped to an oil which was identified as the title compound by spectral analysis and used in Example 67.

Workup

  1. customto come to room temperature
  2. customto give an orange oil
  3. extractionextracted into ethyl ether
  4. washThe ethyl ether was washed with water (100 ml)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered

Sources & evidence

ORD record
ord-8a12a119e2084220a79838395ab692fb
Source dataset
uspto-grants-1985_11
Patent number
US04551279

Reaction notes

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