Triethylamine → HCID 67814333, compound

HRID 2401332Notes

Reaction equation

HRID 2401332 reaction equation
CCN(CC)CC.[C:8]([O:16][CH2:17][C:18]#[CH:19])(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH:20](=[N:22]/[OH:23])\[CH3:21]>C(Cl)(Cl)Cl>[C:8]([O:16][CH2:17][C:18]1[O:23][N:22]=[C:20]([CH3:21])[CH:19]=1)(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 336291Prop-2-yn-1-yl benzoateHCID 5324279(E)-Acetaldehyde oxime

Product 1

HCID 67814333HCID 67814333, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of chloroform, Et3N (0.435 mL, 3.12 mmol), prop-2-ynyl benzoate (1 g, 6.24 mmol), and (E)-acetaldehyde oxime (0.571 mL, 9.37 mmol) at 0° C. was added bleach (23.12 mL, 18.73 mmol). The reaction was stirred overnight before the layers were separated and the aqueous extracted with DCM. The combined organics were dried over Na2SO4, filtered, and concentrated. The crude residue was purified via Biotage (EtOAc/hex) to afford (3-methylisoxazol-5-yl)methyl benzoate. LC/MS m/z 218 [M+H]+.

Workup

  1. customwere separated
  2. extractionthe aqueous extracted with DCM
  3. dry with materialThe combined organics were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue was purified via Biotage (EtOAc/hex)

Sources & evidence

ORD record
ord-ed129a217f5c464fb4ec6010722ca1b1
Source dataset
uspto-grants-2014_08
Patent number
US08796261B2

Reaction notes

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