Triethylamine → HCID 22064315, compound

HRID 891061Notes

Reaction equation

HRID 891061 reaction equation
ClN1C(=O)CCC1=O.[CH:9]1[C:14](/[CH:15]=[N:16]/[OH:17])=[CH:13][CH:12]=[C:11]([F:18])[CH:10]=1.[C:19]([O:22][CH2:23][C:24]#[CH:25])(=[O:21])[CH3:20].C(N(CC)CC)C>C(Cl)Cl>[C:19]([O:22][CH2:23][C:24]1[O:17][N:16]=[C:15]([C:14]2[CH:13]=[CH:12][C:11]([F:18])=[CH:10][CH:9]=2)[CH:25]=1)(=[O:21])[CH3:20]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31398ChlorosuccinimideHCID 69388Propargyl acetateHCID 64360784-Fluorobenzaldehyde oxime

Product 1

HCID 22064315HCID 22064315, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of N-chlorosuccinimide (0.53 g, 4.00 mmol) in methylene chloride (20 mL) was added syn-4-fluorobenzaldoxime (0.56 g, 4.00 mmol) in one portion. The resulting mixture was stirred at room temperature for 3 hours. Propargyl acetate (0.10 g, 1.00 mmol) was then added in one portion, followed by triethylamine (0.28 mL, 2.00 mmol) in methylene chloride (5 mL) over a period of 20 min. The resulting mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure, and the residue was purified by prep-TLC (ethyl acetate:hexanes=1:4) to give [3-(4-fluorophenyl)isoxazol-5-yl]methyl acetate.

Workup

  1. stirringThe resulting mixture was stirred at room temperature overnight
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was purified by prep-TLC (ethyl acetate:hexanes=1:4)

Sources & evidence

ORD record
ord-09346ff1a0334d0495da7fef4499936f
Source dataset
uspto-grants-2006_02
Patent number
US07001909B2

Reaction notes

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