Triethylamine → HCID 18756276, compound

HRID 434058Notes

Reaction equation

HRID 434058 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:9]([I:12])=[CH:8][C:3]=1[C:4](=[N:6][OH:7])Cl.[CH2:13]([O:15][C:16](=[O:20])[C:17]#[C:18][CH3:19])[CH3:14].CCN(CC)CC>CCOCC>[CH2:13]([O:15][C:16]([C:17]1[C:4]([C:3]2[CH:8]=[C:9]([I:12])[CH:10]=[CH:11][C:2]=2[F:1])=[N:6][O:7][C:18]=1[CH3:19])=[O:20])[CH3:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 78043Ethyl 2-butynoateHCID 59119404HCID 59119404, compound

Product 1

HCID 18756276HCID 18756276, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 2-fluoro-5-iodobenzoyl chloride oxime (2.24 g, 7.48 mmol) and ethyl-2-butynoate (1.74 ml, 14.96 mmol, 2 eq.) in Et2O (28 ml) under N2 stirring at 0-5° C., was added dropwise a solution of Et3N (1.35 ml, 9.72 mmol, 1.3 eq) in Et2O (3.6 ml) over 1 h. Reaction was allowed to warm to room temperature and stirred overnight. It was then partitioned between Et2O and H2O, washed with brine, dried (MgSO4), filtered, and concentrated. The crude residue was chromatographed on silica gel using (1-10%) ethyl acetate in hexanes to give the title compound (2.06 g, 73%).

Workup

  1. customReaction
  2. customIt was then partitioned between Et2O and H2O
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude residue was chromatographed on silica gel using (1-10%) ethyl acetate in hexanes

Sources & evidence

ORD record
ord-1c298490bae84337b9920506b24e8dd2
Source dataset
uspto-grants-2003_12
Patent number
US06670373B1

Reaction notes

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