Acetyl chloride → HCID 20252442, compound

HRID 638506Notes

Reaction equation

HRID 638506 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:4]=[CH:5][C:6]([O:9][C:10]2[CH:25]=[CH:24][C:13]([O:14][CH:15]([CH3:23])[CH:16]([OH:22])[CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:12][CH:11]=2)=[N:7][CH:8]=1.[C:28](Cl)(=[O:30])[CH3:29].C(N(CC)CC)C>C(Cl)Cl>[F:27][C:2]([F:26])([F:1])[C:3]1[CH:4]=[CH:5][C:6]([O:9][C:10]2[CH:25]=[CH:24][C:13]([O:14][CH:15]([CH3:23])[CH:16]([O:22][C:28](=[O:30])[CH3:29])[CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:12][CH:11]=2)=[N:7][CH:8]=1

Participants

5

Reactant 3

HCID 6367Acetyl chloride2×HCID 8471Triethylamine2×HCID 179796Methyl 3-hydroxy-4-(4-((5-(trifluoromethyl)-2-pyridinyl)oxy)phenoxy)valerate

Product 1

HCID 20252442HCID 20252442, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5 g of methyl 4-[4-(5-trifluoromethyl-2-pyridyloxy)phenoxy]-3-hydroxypentanoate were dissolved in 35 ml of methylene chloride at 0° C. 0.9 ml of acetyl chloride and then 0.94 ml of triethylamine were added dropwise under nitrogen. After 18.5 hours of standing at room temperature and three hours of reflux, an additional 0.9 ml of acetyl chloride and 0.94 ml of triethylamine were added. The mixture was washed with water dilute acid and brine. The product was purified using silica gel chromatography and identified as the above methyl-3-acetoxy ester.

Workup

  1. temperatureof reflux
  2. washThe mixture was washed with water
  3. additiondilute acid and brine
  4. customThe product was purified

Sources & evidence

ORD record
ord-64337e2d43dc400eac71e1f089bd78b8
Source dataset
uspto-grants-1985_12
Patent number
US04561882

Reaction notes

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