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

HRID 494660Notes

Reaction equation

HRID 494660 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 AcetateYield 75.9%

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) afforded the product as colorless oil (0.12 g, 75%). 1H NMR (300 MHz, CDCl3) δ ppm 0.53 (m, 1H), 0.76 (m, 7H), 1.35 (m, 1H), 1.73 (s, 3H), 1.80 (m, 1H), 2.09 (m, 1H), 3.84 (s, 3H), 4.51 (m, 2H), 5.97 (s, 1H), 7.43 (m, 2H), 7.59 (m, 1H), 8.20 (d, J=7.72 Hz, 1H); 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-03fc5d2187234af9903305d90888ed20
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

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