2-(1-Hexyn-1-yl)-N-methyl-N,4-bis(methyloxy)benzamide → 1-[2-(1-Hexyn-1-yl)-4-(methyloxy)phenyl]-2-phenylethanone

HRID 1992872Notes

Reaction equation

HRID 1992872 reaction equation
[C:1]([C:7]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:8]=1[C:9](N(C)OC)=[O:10])#[C:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH2:21]([Mg]Cl)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1COCC1>[C:1]([C:7]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:8]=1[C:9](=[O:10])[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 860871352-(1-Hexyn-1-yl)-N-methyl-N,4-bis(methyloxy)benzamideHCID 178418336HCID 178418336, compound

Product 1

HCID 685372841-[2-(1-Hexyn-1-yl)-4-(methyloxy)phenyl]-2-phenylethanoneYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2-(1-Hexyn-1-yl)-N-methyl-N,4-bis(methyloxy)benzamide (79) (0.42 g, 1.51 mmol) was dissolved in THF (10 mL). Cooled to 0° C. in an ice bath, benzylmagnesium chloride (2 M in THF, 1.50 mL, 3.0 mmol) was added. The mixture was stirred at 0° C. for 3 h, quenched with saturated aqueous NH4Cl and extracted with EtOAc (2×50 mL). The combined organic extract was washed with brine, dried over Na2SO4, filtered, and the filtrate was concentrated to give the crude product as a yellow oil. The crude product was purified by flash chromatography over SiO2 eluted with a gradient from hexanes to 15% EtOAc in hexanes to give 0.37 g (80%) of the title compound (80) as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 0.93 (t, J=7.3 Hz, 3H), 1.40-1.55 (m, 2H), 1.55-1.65 (m, 2H), 2.46 (t, J=7.2 Hz, 2H), 3.83 (s, 3H), 4.44 (s, 2H), 6.82 (dd, J1=8.8 Hz, J2=2.7 Hz, 1H), 6.96 (d, J=2.5 Hz, 1H), 7.20-7.34 (m, 5H), 7.65 (d, J=8.7 Hz, 1H). LCMS (ESI): m/z 307 (M+H)+.

Workup

  1. customquenched with saturated aqueous NH4Cl
  2. extractionextracted with EtOAc (2×50 mL)
  3. extractionThe combined organic extract
  4. washwas washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated
  8. customto give the crude product as a yellow oil
  9. customThe crude product was purified by flash chromatography over SiO2
  10. washeluted with a gradient from hexanes to 15% EtOAc in hexanes

Sources & evidence

ORD record
ord-6ae2f90322a64136b6b0bb1b5cd5b08d
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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