Dimethylformamide → HCID 21919573, compound

HRID 507713Notes

Reaction equation

HRID 507713 reaction equation
[C:1]1([CH:7]([CH3:11])[C:8](O)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN([CH:15]=[O:16])C.[CH2:17](N(CC)CC)[CH3:18].[CH2:24](Cl)Cl>C(Cl)(=O)C(Cl)=O>[CH2:17]([O:9][C:8]1[C:7]([CH3:11])([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:15](=[O:16])[CH:24]=1)[CH3:18]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 8471TriethylamineHCID 102962-Phenylpropionic acid

Product 1

HCID 21919573HCID 21919573, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 65578Oxalyl chlorideCatalyst

Procedure

A solution of (±) 2-phenylpropionic acid (10.0 g, 0.66 mmol) and DMF (0.3 ml) in DCM (150 ml) was treated dropwise with oxalyl chloride (6.4 ml, 0.72 mmol). After 1 h the reaction mixture was concentrated in vacuo, the residual slurry diluted with Et2O (200 ml) and the resulting precipitate removed by filtration. The filtrate was treated with ethoxyacetylene (40% w/w solution in hexanes, 18 ml) followed dropwise with triethylamine (25 ml, 0.19 mol) and the reaction stirred for 7 d at rt. Filtration and concentration of the filtrate in vacuo followed by chromatography (SiO2, 5:1 EtOAc:hexanes) gave the title compound as a pale yellow oil (6.1 g, 45%). δH (CDCl3, 300K) 7.45-7.24 (5H, m), 5.01 (1H, s), 4.31 (2H, J 7.1 Hz), 1.67 (3H, s), 1.51 (3H, t, J 7.1 Hz); m/z (ES+, 70V) 202.9 (MH+).

Workup

  1. concentrationAfter 1 h the reaction mixture was concentrated in vacuo
  2. additionthe residual slurry diluted with Et2O (200 ml)
  3. customthe resulting precipitate removed by filtration
  4. additionThe filtrate was treated with ethoxyacetylene (40% w/w solution in hexanes, 18 ml)
  5. filtrationFiltration and concentration of the filtrate in vacuo

Sources & evidence

ORD record
ord-8501f9d7464a4a9e939b98c542580924
Source dataset
uspto-grants-2010_08
Patent number
US07786177B2

Reaction notes

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