3-(3,4-Dimethoxyphenyl)-3-methyl-1-nitrobutan-2-ol → 3-(3,4-Dimethoxyphenyl)-3-methyl-1-nitrobutan-2-one

HRID 1627332Notes

Reaction equation

HRID 1627332 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([CH3:19])([CH3:18])[CH:12]([OH:17])[CH2:13][N+:14]([O-:16])=[O:15])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>C(Cl)Cl.CCOCC>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([CH3:19])([CH3:18])[C:12](=[O:17])[CH2:13][N+:14]([O-:16])=[O:15])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 2

HCID 667407963-(3,4-Dimethoxyphenyl)-3-methyl-1-nitrobutan-2-olHCID 178418287HCID 178418287, compound2×

Product 1

HCID 866622423-(3,4-Dimethoxyphenyl)-3-methyl-1-nitrobutan-2-oneYield 72.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(3,4-dimethoxyphenyl)-3-methyl-1-nitrobutan-2-ol (700 mg, 2.60 mmol) in DCM (30 mL) were added PCC (3.36 g, 15.60 mmol) and Celite (3.36 g). After stirring 48 h, additional PCC (3.36 g, 15.60 mmol) and Celite (3.36 g) were added. After stirring further for 24 h, the mixture was diluted with Et2O and filtered. The filtrate was concentrated and purified by flash chromatography to afford 3-(3,4-dimethoxyphenyl)-3-methyl-1-nitrobutan-2-one (502 mg, 72%). 1H NMR (400 MHz, CDCl3) δ 6.91-6.84 (m, 2H), 6.69 (s, 1H), 5.13 (s, 2H), 3.90 (s, 3H), 3.89 (s, 3H), 1.56 (s, 6H).

Workup

  1. stirringAfter stirring further for 24 h
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. custompurified by flash chromatography

Sources & evidence

ORD record
ord-8ee5cbc94ba24faf99472433cef2f70e
Source dataset
uspto-grants-2014_07
Patent number
US08785488B2

Reaction notes

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