Dimethylformamide → HCID 21919573, compound

HRID 1991042Notes

Reaction equation

HRID 1991042 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-093e38db5106405a96b1db0555a4c773
Source dataset
uspto-grants-2010_01
Patent number
US07645770B2

Reaction notes

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