HCID 12088903, compound → 4-Ethyl-6-methoxy-1,1,7-trimethyl-1,2-dihydronaphthalene

HRID 1795579Notes

Reaction equation

HRID 1795579 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([CH3:15])([CH3:14])[CH2:8][CH2:9][C:10]2=O)=[CH:5][C:4]=1[CH3:16].[CH3:17][CH2:18][Mg+].[Br-]>>[CH2:17]([C:10]1[C:11]2[C:6](=[CH:5][C:4]([CH3:16])=[C:3]([O:2][CH3:1])[CH:12]=2)[C:7]([CH3:15])([CH3:14])[CH2:8][CH:9]=1)[CH3:18]

Participants

3

Reactant 2

HCID 12088903HCID 12088903, compound2×HCID 178461630HCID 178461630, compound

Product 1

HCID 222183394-Ethyl-6-methoxy-1,1,7-trimethyl-1,2-dihydronaphthaleneYield 63%

Procedure

Following General Procedure A, 7-methoxy-4,4,6-trimethyl-3,4-dihydro-2H-naphthalen-1-one (Compound 6, 0.5 g, 2.3 mmol) was reacted with a solution of 3 M EtMgBr (2.3 mL, 6.9 mmol), and the crude product was purified by flash chromatography (hexane:ethyl acetate=4:1) to give 0.33 g (63%) of the title compound as a clear oil. PNMR (300 MHz, CDCl3) δ 1.32 (t,3 H, J=6.3 Hz), 1.38 (s, 6 H), 2.32 (d, 2 H, J=4.5 Hz), 2.42 (s, 3 H), 2.65 (m, 2 H), 3.98 (s, 3 H), 5.88 (t, 1 H, J=2.5 Hz), 6.96 (s, 1 H), 7.28 (s, 1 H).

Workup

  1. customthe crude product was purified by flash chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-05e3082eaa6f4806a72c861035955967
Source dataset
uspto-grants-2006_04
Patent number
US07026487B2

Reaction notes

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