Water → 3-Methoxy-4-(3-methylbutyl)-4-vinylnaphthalen-1(4h)-one

HRID 494667Notes

Reaction equation

HRID 494667 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH2:15][CH2:16][CH:17]([CH3:19])[CH3:18])([CH:13]=[CH2:14])[C:5]2[C:10]([CH2:11][CH:12]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=[O:21].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.C(OOC(C)(C)C)(C)(C)C.O>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[C:4]([CH2:15][CH2:16][CH:17]([CH3:19])[CH3:18])([CH:13]=[CH2:14])[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:11](=[O:21])[CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8033Di-tert-butyl peroxideHCID 2724130Cornforth reagentHCID 688756232-Methoxy-1-(3-methylbutyl)-1-vinyl-1,4-dihydronaphthalene

Product 1

HCID 688721423-Methoxy-4-(3-methylbutyl)-4-vinylnaphthalen-1(4h)-oneYield 35%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of Example 181B (0.13 g, 0.5 mmol) in benzene (5 mL) was added celite (0.13 g), pyridinium dichromate (0.38 g, 1.0 mmol), and a solution of 70% t-butyl peroxide in water (0.13 mL, 1.0 mmol). The heterogenous solution was filtered through celite. The filtrate was diluted with ethyl acetate (10 mL), washed with 5% Na2S2O5 (10 mL), dried (Na2SO4), and concentrated in vacuo. Column Chromatography on silica (20% dichloromethane/hexane -15% ethyl acetate/hexane) afforded product as a light yellow oil (46 mg, 35%). 1H NMR (300 MHz, CDCl3) δ ppm 0.51 (m, 1H), 0.76 (m, 7H), 1.37 (m, 1 H), 2.01 (m, 1H), 2.33 (m, 1H), 3.81 (s, 3H), 5.12 (m, 2H), 5.94 (m, 2H), 7.37 (m, 2H), 7.54 (m, 1H), 8.18 (d, J=8.09 Hz, 1H); MS m/z 270.9 (M+H)+.

Workup

  1. filtrationThe heterogenous solution was filtered through celite
  2. additionThe filtrate was diluted with ethyl acetate (10 mL)
  3. washwashed with 5% Na2S2O5 (10 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a05bf35c32f444458c590343a496a377
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

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