Hydrochloric Acid → Methyl 1-oxodecahydronaphthalene-2-carboxylate

HRID 2059721Notes

Reaction equation

HRID 2059721 reaction equation
[H-].[Na+].[C:3](=[O:8])([O:6][CH3:7])OC.[C:9]1(=[O:19])[CH:18]2[CH:13]([CH2:14][CH2:15][CH2:16][CH2:17]2)[CH2:12][CH2:11][CH2:10]1.Cl>O1CCCC1.CCOCC>[O:19]=[C:9]1[CH:18]2[CH:13]([CH2:14][CH2:15][CH2:16][CH2:17]2)[CH2:12][CH2:11][CH:10]1[C:3]([O:6][CH3:7])=[O:8]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 12021Dimethyl CarbonateHCID 24758Sodium hydrideHCID 98501Bicyclo[4.4.0]decan-1-one

Product 1

HCID 68799034Methyl 1-oxodecahydronaphthalene-2-carboxylate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of sodium hydride (4.60 g, 115 mmol) in tetrahydrofuran (20 mL) was treated with dimethyl carbonate (8.29 mL, 99 mmol), heated to reflux under nitrogen, treated dropwise with a solution of octahydronaphthalen-1(2H)-one (Aldrich cat#115063, mixture of trans (major) and cis (minor), 5 g, 32.8 mmol) in tetrahydrofuran (20 mL) over 5 minutes, and heated to reflux overnight. The mixture was cooled, diluted with ether (300 mL) and treated with 1 M hydrochloric acid (150 mL). The layers were separated and the aqueous layer was extracted with ether (2×100 mL). The combined ether layers were washed with brine, dried (magnesium sulfate), filtered and concentrated to provide the desired product that was not purified, but used as is in the next step.

Workup

  1. temperatureheated
  2. temperatureto reflux under nitrogen
  3. temperatureheated
  4. temperatureto reflux overnight
  5. temperatureThe mixture was cooled
  6. customThe layers were separated
  7. extractionthe aqueous layer was extracted with ether (2×100 mL)
  8. washThe combined ether layers were washed with brine
  9. dry with materialdried (magnesium sulfate)
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-9e5624f377624a6cbff153162646725b
Source dataset
uspto-grants-2012_10
Patent number
US08278311B2

Reaction notes

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