Dimethylformamide → 2-Methylpentane

HRID 2234173Notes

Reaction equation

HRID 2234173 reaction equation
[CH2:1]([O:9][CH2:10][CH2:11][C:12]([OH:14])=O)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:15](Cl)(=[O:19])[C:16](Cl)=O.[CH3:21][N:22]([CH3:25])C=O>ClCCl>[CH3:6][CH2:5][CH2:4][CH:3]([CH3:8])[CH3:2].[CH2:1]([O:9][CH:10]([O:19][CH2:15][CH3:16])[CH2:25][N:22]([C:21]1[CH:7]=[CH:8][CH:3]=[CH:4][CH:5]=1)[C:12](=[O:14])[CH2:11][CH2:10][O:9][CH2:1][CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)[CH3:2]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 154386723-(2-Phenylethoxy)propanoic acid

Product 2

HCID 78922-MethylpentaneHCID 68702196N-(2,2-Diethoxyethyl)-3-phenethyloxy-N-phenyl-propanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Phenethyloxypropanoic acid (0.25 g) was dissolved in dichloromethane (8 mL) and treated with oxalyl chloride (0.22 g) and a drop of dimethylformamide at ambient temperature. The resultant solution was stirred at ambient temperature for 1 hour. The solution was then concentrated and azeotroped with dichloromethane (3×8 mL). The collected residue was dissolved in dichloromethane (8 mL) and added to a stirred solution of N-(2,2-diethoxyethyl)aniline (0.27 g) and N-ethyl-N-isopropyl-propan-2-amine (0.4 mL), dissolved in dichloromethane (4 mL), at ambient temperature. The resultant solution was stirred at ambient temperature for 1 hour. The mixture was then poured into ethyl acetate (25 mL), washed with water (2×25 mL), washed with brine (25 mL), dried over anhydrous magnesium sulphate, filtered and concentrated. The collected residue was purified by flash chromatography eluting with 1:6 ethylacetate:iso-hexane to yield the sub-titled compound (0.18 g) as an oil.

Workup

  1. customat ambient temperature
  2. concentrationThe solution was then concentrated
  3. customazeotroped with dichloromethane (3×8 mL)
  4. dissolutionThe collected residue was dissolved in dichloromethane (8 mL)
  5. additionadded to a stirred solution of N-(2,2-diethoxyethyl)aniline (0.27 g) and N-ethyl-N-isopropyl-propan-2-amine (0.4 mL)
  6. dissolutiondissolved in dichloromethane (4 mL), at ambient temperature
  7. additionThe mixture was then poured into ethyl acetate (25 mL)
  8. washwashed with water (2×25 mL)
  9. washwashed with brine (25 mL)
  10. dry with materialdried over anhydrous magnesium sulphate
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customThe collected residue was purified by flash chromatography
  14. washeluting with 1:6 ethylacetate

Sources & evidence

ORD record
ord-72de01bcc3f24854b378cf47c97ccda5
Source dataset
uspto-grants-2010_05
Patent number
US07709511B2

Reaction notes

Loading…