Hydrochloric Acid → Methyl 1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate

HRID 1027878Notes

Reaction equation

HRID 1027878 reaction equation
[H-].[Na+].[CH2:3]1[CH2:13][C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4]1.Cl.[C:15](=O)([O:18]C)[O:16][CH3:17]>>[CH3:17][O:16][C:15]([CH:13]1[CH2:3][CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:11]1=[O:12])=[O:18]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 107241-TetraloneHCID 12021Dimethyl CarbonateHCID 24758Sodium hydride

Product 1

HCID 344494Methyl 1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate

Conditions

Temperature
90 °C

Procedure

A suspension of 60% dispersion of sodium hydride in mineral oil (1.64 g, 41 mmol) in dimethyl carbonate (50 mL) was treated dropwise with alpha-tetralone (4.6 mL, 34 mmol). The mixture was heated at 90° C. for 20 minutes, cooled to ambient temperature, treated with 2 M HCl (40 mL), and extracted with EtOAc (100 mL and 25 mL). The combined EtOAc layers were washed with brine, dried (MgSO4), filtered, concentrated under reduced pressure and chromatographed on silica gel eluting with a gradient of hexane:EtOAc (20:1 and 10:1) to provide the title compound. MS (M+H)+ m/z 205.

Workup

  1. temperaturecooled to ambient temperature
  2. extractionextracted with EtOAc (100 mL and 25 mL)
  3. washThe combined EtOAc layers were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customchromatographed on silica gel eluting with a gradient of hexane:EtOAc (20:1 and 10:1)

Sources & evidence

ORD record
ord-83a4c15a26f744f5be47e5e1f4f4c993
Source dataset
uspto-grants-2014_05
Patent number
US08735411B2

Reaction notes

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