1-Tetralone → Methyl 1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate

HRID 2039728Notes

Reaction equation

HRID 2039728 reaction equation
[H-].[Na+].[C:3](=[O:8])([O:6][CH3:7])OC.[C:9]1(=[O:19])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11][CH2:10]1>>[O:19]=[C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11][CH:10]1[C:3]([O:6][CH3:7])=[O:8]

Participants

4

Reactant 3

HCID 107241-TetraloneHCID 12021Dimethyl CarbonateHCID 24758Sodium hydride

Product 1

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

Conditions

Temperature
80 °C

Procedure

Under an argon atmosphere, a mixture of sodium hydride (60% dispersion in mineral oil, 887 mg, 22.0 mmol), dimethyl carbonate (15 mL) and 3,4-dihydronaphthalen-1(2H)-one (1.46 g, 10.0 mmol) was stirred at 80° C. for 3.5 hr. The reaction mixture was quenched with diluted hydrochloric acid, and extracted with ethyl acetate. The organic layer was dried over sodium carbonate, filtrated, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=1/0→5/1) to give the title compound as a white solid.

Workup

  1. customThe reaction mixture was quenched with diluted hydrochloric acid
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium carbonate
  4. filtrationfiltrated
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=1/0→5/1)

Sources & evidence

ORD record
ord-1421e3507aac48fd839c8d8a21a889da
Source dataset
uspto-grants-2013_11
Patent number
US08580804B2

Reaction notes

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