2,4-Dichloro-N-methoxy-N-methylbenzamide → 2',4'-Dichlorovalerophenone

HRID 1671327Notes

Reaction equation

HRID 1671327 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9](N(OC)C)=[O:10].[Li][CH2:16][CH2:17][CH2:18][CH3:19]>C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:10])[CH2:16][CH2:17][CH2:18][CH3:19]

Participants

4

Reactant 2

HCID 118453452,4-Dichloro-N-methoxy-N-methylbenzamideHCID 178418339Butyllithium

Product 1

HCID 109880862',4'-Dichlorovalerophenone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring hazy solution of 2,4-dichloro-N-methoxy-N-methylbenzenecarboxamide (1 g, 4.27 mmol), in THF (20 ml) is added BuLi (2.051 ml, 5.13 mmol) in portions. The reaction is stirred for 4 hours at RT and the partitioned between 1M HCl (100 ml) and EtOAc (140 ml). The organic portion is washed with brine, dried over Na2SO4, and concentrated in vacuo. The crude product is purified by ISCO combiflash chromatography eluting with 0 to 100% EtOAc/iso-hexane on a 40 g silica-column to yield 1-(2,4-dichloro-phenyl)-pentan-1-one as a brown oil; 1H NMR (400 MHz, CDCl3) δ 7.45 (1H, d, J 2.0), 7.43 (1H, d, J 7.3), 7.32 (1H, dd, J 7.3, 2.0), 2.94 (2H, t, J 7.4), 1.70 (2H, m), 1.40 (2H, m), 0.95 (3H, t, J 7.3).

Workup

  1. customthe partitioned between 1M HCl (100 ml) and EtOAc (140 ml)
  2. washThe organic portion is washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product is purified by ISCO combiflash chromatography
  6. washeluting with 0 to 100% EtOAc/iso-hexane on a 40 g silica-column

Sources & evidence

ORD record
ord-9bf9e07a4e094765acf3743e102ad69e
Source dataset
uspto-grants-2011_08
Patent number
US07994203B2

Reaction notes

Loading…