Water → [2-methoxy-1-(3-methylbutyl)-4-oxo-1,4-dihydronaphthalen-1-yl]methyl Acetate

HRID 2224980Notes

Reaction equation

HRID 2224980 reaction equation
[C:1]([O:4][CH2:5][C:6]1([CH2:18][CH2:19][CH:20]([CH3:22])[CH3:21])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][CH:8]=[C:7]1[O:16][CH3:17])(=[O:3])[CH3:2].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=[O:24].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.C(OOC(C)(C)C)(C)(C)C.O>C1C=CC=CC=1>[C:1]([O:4][CH2:5][C:6]1([CH2:18][CH2:19][CH:20]([CH3:22])[CH3:21])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=[O:24])[CH:8]=[C:7]1[O:16][CH3:17])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8033Di-tert-butyl peroxideHCID 2724130Cornforth reagentHCID 68872462[2-Methoxy-1-(3-methylbutyl)-1,4-dihydronaphthalen-1-yl]methyl acetate

Product 1

HCID 68873688[2-methoxy-1-(3-methylbutyl)-4-oxo-1,4-dihydronaphthalen-1-yl]methyl Acetate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of Example 179B (0.15 g, 0.5 mmol) in benzene (5 mL) was added celite (0.15 g), pyridinium dichromate (0.75 g, 2.0 mmol), and a solution of 70% t-butyl peroxide in water (0.25 mL, 2.0 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 (5% to 15% ethyl acetate/hexane gradient) affored the product as colorless oil (0.12 g, 75%). 1H NMR (300 MHz, CDCl3) δ ppm 0.53 (m, 1 H), 0.76 (m, 7 H), 1.35 (m, 1 H), 1.73 (s, 3 H), 1.80 (m, 1 H), 2.09 (m, 1 H), 3.84 (s, 3 H), 4.51 (m, 2 H), 5.97 (s, 1 H), 7.43 (m, 2 H), 7.59 (m, 1 H), 8.20 (d, J=7.72 Hz, 1 H); MS m/z 317.1 (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-7181f097344c4d1d885a43a73ee9c3f7
Source dataset
uspto-grants-2008_05
Patent number
US07378414B2

Reaction notes

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