Cyclooctanone → Ethyl 2-oxocyclononanecarboxylate

HRID 5389

Reaction equation

[C:1]1(=[O:9])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.F[B-](F)(F)F.C([O+](CC)CC)C.[N+](=[CH:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[N-]>C(Cl)Cl>[CH2:28]([O:27][C:25]([CH:24]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:1]1=[O:9])=[O:26])[CH3:29]

Participants

Conditions

Temperature: 0 °C

Procedure

Cyclooctanone (25 g, 198 mmol) is dissolved in methylene chloride (500 mL) and the solution is cooled to 0° C. Triethyloxonium tetrafluoroborate (121.6 g, 640 mmol) is added. Ethyl diazoacetate (41.61 g, 365 mmol) is then added dropwise over 25 minutes, and the reaction is stirred at 0° C. for 4 hours. The reaction is quenched by pouring into a solution of sodium bicarbonate (160 g) in water (1.6 L) and stirring overnight. The reaction mixture is then extracted several times with methylene chloride, the combined organic layers are dried (Na2SO4), and the solvent is evaporated. The product is purified by vacuum distillation (0.2-1.0 mm Hg) and the fraction boiling between 100°-125° C. is collected to give 2-ethoxycarbonyl-cyclononanone.

Workup

customThe reaction is quenched
additionby pouring into a solution of sodium bicarbonate (160 g) in water (1.6 L)
stirringstirring overnight
extractionThe reaction mixture is then extracted several times with methylene chloride
dry with materialthe combined organic layers are dried (Na2SO4)
customthe solvent is evaporated
distillationThe product is purified by vacuum distillation (0.2-1.0 mm Hg)
customboiling between 100°-125° C.
customis collected

Sources & evidence

ORD record: ord-e3905ec671db4476912df221b80d4a05
Source dataset: uspto-grants-1993_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05244889

Linked notes

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