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

HRID 494663Notes

Reaction equation

HRID 494663 reaction equation
[CH:1]([NH:4][C:5](=[O:25])[O:6][CH2:7][C:8]1([CH2:20][CH2:21][CH:22]([CH3:24])[CH3:23])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH:10]=[C:9]1[O:18][CH3:19])([CH3:3])[CH3:2].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=[O:27].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.C(OOC(C)(C)C)(C)(C)C.O>C1C=CC=CC=1>[CH:1]([NH:4][C:5](=[O:25])[O:6][CH2:7][C:8]1([CH2:20][CH2:21][CH:22]([CH3:24])[CH3:23])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11](=[O:27])[CH:10]=[C:9]1[O:18][CH3:19])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8033Di-tert-butyl peroxideHCID 2724130Cornforth reagentHCID 68871317[2-Methoxy-1-(3-methylbutyl)-1,4-dihydronaphthalen-1-yl]methyl isopropylcarbamate

Product 1

HCID 68874679[2-methoxy-1-(3-methylbutyl)-4-oxo-1,4-dihydronaphthalen-1-yl]methyl IsopropylcarbamateYield 83.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of Example 180A (39 mg, 0.11 mmol) in benzene (1 mL) was added celite (39 mg), pyridinium dichromate (0.17 g, 0.45 mmol), and a solution of 70% t-butyl peroxide in water (58 μL, 0.45 mmol). The heterogenous solution was filtered through celite. The filtrate was diluted with ethyl acetate (3 mL), washed with 5% Na2S2O5 (3 mL), dried (Na2SO4), and concentrated in vacuo. Column chromatography on silica (10%-20% ethyl acetate/hexane) afforded product as a white solid (33 mg, 83%). 1H NMR (300 MHz, CDCl3) δ ppm 0.53 (m, 1H), 0.75 (m, 7H), 0.93 (d, J=5.88 Hz, 3H), 1.03 (d, J=5.88 Hz, 3H), 1.34 (m, 1H), 1.79 (m, 1H), 2.08 (m, 1H), 3.84 (s, 3H), 4.13 (m, 1H), 4.41 (d, J=10.30 Hz, 2H), 4.57 (m, 1H), 5.96 (s, 1H), 7.43 (m, 2H), 7.59 (m, 1H), 8.19 (d, J=7.72 Hz, 1H).

Workup

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

Sources & evidence

ORD record
ord-464f285a3f9c4cafbd556af85e497ce8
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

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