Methyl iodide → 7-Methoxy-1,1-dimethyl-3,4-dihydronaphthalen-2(1H)-one

HRID 2300958Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][C:9](=[O:14])[CH:10]2[CH3:13])=[CH:5][CH:4]=1.I[CH3:16].OS([O-])(=O)=O.[K+]>C1COCC1.[Cl-].[Na+].O>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][C:9](=[O:14])[C:10]2([CH3:16])[CH3:13])=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 7-methoxy-1-methyl-3,4-dihydro-1H-naphthalen-2-one (1.95 g, 10.3 mmol) in THF (30 ml) was added NHMDS (11.3 mmol, 11.3 ml, 1M in THF) at 0° C. under nitrogen. The resulted solution was stirred at 0° C. for 1 hr. Iodomethane (7.29 g, 3.19 ml, 51.3 mmol) was added and stirred for an additional 3 hrs. 10% KHSO4 aqueous solution was added to acidify the reaction mixture, diluted with brine, extracted with ethylacetate, washed with brine, dried over MgSO4, filtered. The filtrate was evaporated under vacuo. The residue was purified by chromatography using ethylacetate:hexane (0.9:9.5) as eluant to give the desired product as white solid. (1.77 g, 85%). 1H NMR (CDCl3) δ: 7.08(d, 1H, J=8.3 Hz), 6.88(d, 1H, J=2.7 Hz), 6.74(dd, 1H, J=2.7 and 8.3 Hz), 3.80(s, 3H), 3.03(t, 2H, J=6.6 Hz), 2.65(t, 2H, J=6.6 Hz), 1.42(s, 6H). 13C NMR (CDCl3) δ: 213.7, 157.8, 143.9, 128.1, 126.5, 111.3, 110.4, 54.4, 46.9, 36.5, 26.8, 25.8.

Workup

stirringstirred for an additional 3 hrs
extractionextracted with ethylacetate
washwashed with brine
dry with materialdried over MgSO4
filtrationfiltered
customThe filtrate was evaporated under vacuo
customThe residue was purified by chromatography

Sources & evidence

ORD record: ord-edbe987f264a4089aa0166424361c9e9
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06498196B1

Reaction notes

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