Ethyl Acetate → 1-(2,4-Dichloro-phenyl)-3-methyl-butan-1-one

HRID 1671326Notes

Reaction equation

HRID 1671326 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([OH:14])[CH2:10][CH:11]([CH3:13])[CH3:12].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.CCOC(C)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:14])[CH2:10][CH:11]([CH3:12])[CH3:13]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 159087TriacetoxyperiodinaneHCID 61271586(2,4-Dichloro-phenyl)-3-methyl-butan-1-ol

Product 1

HCID 612724331-(2,4-Dichloro-phenyl)-3-methyl-butan-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(2,4-Dichloro-phenyl)-3-methyl-butan-1-ol (600 mg, 2.57 mmol) and Dess-Martin periodinane (1092 mg, 2.57 mmol) in DCM (25 ml) is stirred at RT for 2 hours. The reaction mixture is added to EtOAc (200 ml) and washed with sat. sodium metabisulfite (200 ml), sat. NaHCO3 (200 ml), brine, dried over MgSO4 and concentrated in vacuo. The crude product is purified using an ISCO combiflash chromatography, eluting with 0 to 100% (EtOAc/iso-hexane) on a 40 g silica-column to give 1-(2,4-Dichloro-phenyl)-3-methyl-butan-1-one as a yellow oil; 1H NMR (400 MHz, CDCl3) δ 7.45 (1H, d, J 1.9), 7.42 (1H, d, J 8.3), 7.32 (1H, dd, J 8.3, 1.9), 2.83 (2H, d, J 6.9), 2.25 (1H, sept, J 6.7), 1.00 (6H, d, J 6.7).

Workup

  1. washwashed with sat. sodium metabisulfite (200 ml), sat. NaHCO3 (200 ml), brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe crude product is purified
  5. washeluting with 0 to 100% (EtOAc/iso-hexane) on a 40 g silica-column

Sources & evidence

ORD record
ord-a3eaef64ca7f49afbbc638694cf50591
Source dataset
uspto-grants-2011_08
Patent number
US07994203B2

Reaction notes

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