HCID 22218197, compound → HCID 22218199, compound

HRID 1166651Notes

Reaction equation

HRID 1166651 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[CH3:13])[C:9](=O)[CH2:8][CH2:7][C:6]2([CH3:16])[CH3:15].[CH3:17][CH2:18][Mg+].[Br-]>>[CH2:17]([C:9]1[C:10]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[C:12]([CH3:13])[CH:11]=2)[C:6]([CH3:16])([CH3:15])[CH2:7][CH:8]=1)[CH3:18]

Participants

3

Reactant 2

HCID 22218197HCID 22218197, compound2×HCID 178461630HCID 178461630, compound

Product 1

HCID 22218199HCID 22218199, compoundYield 40%

Procedure

Following General Procedure F, 6-methoxy-4,4,7-trimethyl-3,4-dihydro-2H-naphthalen-1-one (compound 30, 1.0 g, 4.6 mmol) was reacted with a solution of 3M EtMgBr (8 mL, 23.0 mmol), and the crude product was purified by flash column (hexane:ethyl acetate=96:4) to give 0.42 g (40%) of the title compound as a clear oil. PNMR (300 MHz, CDCl3) δ 1.36 (t, 3H, J=6.0 Hz), 1.46 (s, 6H), 2.35 (d, 2H, J=4.5 Hz), 2.42 (s, 3H), 2.65 (q, 2H, J=7.5 Hz), 4.03 (s, 3H), 5.82 (t, 1H, J=2.5 Hz), 7.02 (s, 1H), 7.28 (s, 1H).

Workup

  1. customthe crude product was purified by flash column (hexane:ethyl acetate=96:4)

Sources & evidence

ORD record
ord-a0e3871d90d54e4dbcc05d59920bf83c
Source dataset
uspto-grants-2003_09
Patent number
US06613917B1

Reaction notes

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