Dimethylformamide → HCID 21919639, compound

HRID 966406Notes

Reaction equation

HRID 966406 reaction equation
CN([CH:4]=[O:5])C.[C:6](Cl)(=[O:10])[C:7](Cl)=O.[CH2:12]([O:14][C:15]#[CH:16])[CH3:13].C(N([CH2:22][CH3:23])CC)C.[CH2:24](Cl)Cl>>[CH2:15]([O:14][C:12]1[C:24]2([CH2:7][CH2:6][O:10][CH2:23][CH2:22]2)[C:4](=[O:5])[CH:13]=1)[CH3:16]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 8471TriethylamineHCID 61239Ether, ethyl ethynylHCID 65578Oxalyl chloride

Product 1

HCID 21919639HCID 21919639, compoundYield 59%

Procedure

Tetrahydropyranyl-4-carboxylic acid (14.7 g, 0.11 mol) and DMF (0.5 ml) in DCM (150 ml) was treated dropwise with oxalyl chloride (1.1 eq, 10.9 ml, 0.12 mol). After 1 h the reaction mixture was concentrated in vacuo and the residual slurry was diluted with Et2O (200 ml) and the resulting precipitate removed by filtration. The filtrate was treated with ethoxyacetylene (40% w/w solution in hexanes, 1.3 eq, 18 ml) followed dropwise with triethylamine (25 ml, 0.19 mol) and the reaction stirred for 11 d. 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 (12.1 g, 59%). δH (CDCl3, 300K) 4.85 (1H, s), 4.23 (2H, q, J 7.1 Hz), 3.89-3.75 (4H, m), 1.88-1.79 (4H, m), 1.47 (3H, t, J 7.1 Hz); m/z (ES+, 70V) 182.9 (MH+).

Workup

  1. concentrationAfter 1 h the reaction mixture was concentrated in vacuo
  2. additionthe residual slurry was diluted with Et2O (200 ml)
  3. customthe resulting precipitate removed by filtration
  4. filtrationFiltration and concentration of the filtrate in vacuo

Sources & evidence

ORD record
ord-b11e8b3940a640ecb25b3298316d2834
Source dataset
uspto-grants-2005_10
Patent number
US06951943B2

Reaction notes

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