6-Methoxy-alpha-tetralone → HCID 22667820, compound

HRID 1007137Notes

Reaction equation

HRID 1007137 reaction equation
[CH3:1][Li].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11](=O)[CH2:10][CH2:9][CH2:8]2>C1COCC1.C(OCC)(=O)C>[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH:11]([CH3:1])[CH2:10][CH:9]=[CH:8]2

Participants

5

Reactant 2

HCID 141126-Methoxy-alpha-tetraloneHCID 178418348HCID 178418348, compound

Product 1

HCID 22667820HCID 22667820, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyllithium (1M solution in THF; 27 ml, 27 mmol) was added slowly to a solution of 6-methoxy-1-tetralone (3.16 g, 18 mmol) in THF (15 ml) under N2. The reaction mixture was allowed to react under N2 at RT overnight (12 h). It was then diluted with ethyl acetate and quenched with ice-cooled HCl (2M). The aqeous phase was extracted further with ethyl acetate, dried, and concentrated in vacuo. Chromatographic purification of the crude material on silica gel, using 5% ether in petroleum ether as eluent, gave the title compound as a gum (1.6 g, 52%). 1H-NMR (250 MHz CDCl3): 2.1 (t, 3H, Me), 2.2 (m, 2H), 2.8 (t, 2H), 3.8 (s, 3H, OMe), 5.8 (t, 1H), 6.8-7.2 (m, 3H), 13C-NMR (250 MHz, CDCl3) 19.3, 23.2, 28.9, 55.2, 110.8, 113.7, 122.9, 123.9, 129.1, 131.8, 138.1, 158.4; Mass Spectrum (M+1) m/e=175.

Workup

  1. customto react under N2 at RT overnight (12 h)
  2. customquenched with ice-
  3. temperaturecooled HCl (2M)
  4. extractionThe aqeous phase was extracted further with ethyl acetate
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customChromatographic purification of the crude material on silica gel

Sources & evidence

ORD record
ord-872313f346764841a75264f1d6645cd2
Source dataset
uspto-grants-2004_09
Patent number
US06794384B1

Reaction notes

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