Potassium Carbonate → 2-[2-(Tert-butoxycarbonyl)ethyl]-2-ethoxycarbonylcyclohexanone

HRID 861703Notes

Reaction equation

HRID 861703 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][C:7]1=[O:12])=[O:5])[CH3:2].[C:13]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])(=[O:16])[CH:14]=[CH2:15].C(=O)([O-])[O-].[K+].[K+]>C(O)(C)(C)C.ClCCl>[C:18]([O:17][C:13]([CH2:14][CH2:15][C:6]1([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:11][CH2:10][CH2:9][CH2:8][C:7]1=[O:12])=[O:16])([CH3:21])([CH3:20])[CH3:19]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 15458tert-Butyl acrylateHCID 95543Ethyl 2-oxocyclohexanecarboxylate

Product 1

HCID 190674782-[2-(Tert-butoxycarbonyl)ethyl]-2-ethoxycarbonylcyclohexanone

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6386tert-ButanolSolvent

Procedure

To a solution of 2-ethoxycarbonylcyclohexanone (5.0 g, 0.029 mol) and tert-butyl acrylate (4.83 g, 0.037 mol) in tert-butanol (30 ml) was added, in one portion, potassium carbonate (4.0 g, 0.029 mol). The suspension was stirred at room temperature for 22 hours, diluted with dichloromethane (100 ml) and distilled water (100 ml) and the layers separated. The aqueous layer was extracted with dichloromethane (2×100 ml) and the combined dichloromethane extracts dried over magnesium sulphate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on silica by eluting with hexane/ethyl acetate (4:1) to give, after combination and evaporation of appropriate fractions, the title compound as a colorless oil, (7.99 g, 92.3%; 98.92% by GC normalization) (MH+ 299.03, 8.53%). Rf. 0.15 (silica, hexane/ethyl acetate 4:1). 1H-NMR (300 MHz, CDCl3):=1.20 (t, 3H), 1.37 (s, 9H), 1.52-2.46 (m, 12H), 4.08-4.21 (m, 2H) ppm. 13C-NMR (62 MHz, CDCl3):=13.97, 22.38, 27.36, 27.91, 29.52, 30.49, 36.06, 40.85, 59.87, 61.19, 80.10, 171.61, 172.22, 207.39 ppm. Analysis %: Found: C, 64.19; H, 8.80; C16H26O5 requires: C, 64.41; H, 8.78.

Workup

  1. distillationdistilled water (100 ml)
  2. customthe layers separated
  3. extractionThe aqueous layer was extracted with dichloromethane (2×100 ml)
  4. dry with materialthe combined dichloromethane extracts dried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by chromatography on silica
  8. washby eluting with hexane/ethyl acetate (4:1)
  9. customto give
  10. customafter combination and evaporation of appropriate fractions

Sources & evidence

ORD record
ord-c2432f3c4c054247beedcf8536c9bb13
Source dataset
uspto-grants-1998_02
Patent number
US05714628

Reaction notes

Loading…