Hydrochloric Acid → Ethyl cyclooctylideneacetate

HRID 2223830Notes

Reaction equation

HRID 2223830 reaction equation
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.[C:17]1(=O)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.Cl>O1CCCC1.O>[C:17]1(=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10403CyclooctanoneHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydride

Product 1

HCID 14002565Ethyl cyclooctylideneacetate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 60% sodium hydride/mineral oil (969 mg) in tetrahydrofuran (50 mL) was added ethyl diethylphosphonoacetate (5.48 mL) dropwise under ice cooling. After stirring the solution under ice cooling for 30 minutes, a solution of cyclooctanone (2.52 g) in tetrahydrofuran (70 mL) was added dropwise to the solution under ice cooling. The resulting solution was stirred under ice cooling for 2 hours and at room temperature for 40 hours. Water and 3N hydrochloric acid were then added to the solution, and the mixture was extracted with diethyl ether. The organic layer was washed with water and saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and then, concentrated under reduced pressure. The resulting residue was purified by chromatography (silica gel, hexane:ethyl acetate=9:1) to give the title compound (1.96 g)

Workup

  1. stirringThe resulting solution was stirred under ice cooling for 2 hours and at room temperature for 40 hours
  2. extractionthe mixture was extracted with diethyl ether
  3. washThe organic layer was washed with water and saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by chromatography (silica gel, hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-92fd520c7c484cb5bd22c23f6501417f
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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