Ethyl Acetate → HCID 131717577, compound

HRID 466474Notes

Reaction equation

HRID 466474 reaction equation
[C:1]([CH2:3][C:4]1[C:5]([CH2:21][CH:22]([CH3:24])[CH3:23])=[C:6]([C:17]([O:19][CH3:20])=[O:18])[C:7]([CH:14]([F:16])[F:15])=[N:8][C:9]=1[C:10]([F:13])([F:12])[F:11])#[N:2].Cl[C:26]([O:28][CH2:29][CH2:30]Br)=[O:27].[OH-].[Na+].C(OCC)(=O)C>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.ClCCl>[C:1]([C:3](=[C:26]1[O:28][CH2:29][CH2:30][O:27]1)[C:4]1[C:5]([CH2:21][CH:22]([CH3:24])[CH3:23])=[C:6]([C:17]([O:19][CH3:20])=[O:18])[C:7]([CH:14]([F:16])[F:15])=[N:8][C:9]=1[C:10]([F:12])([F:13])[F:11])#[N:2]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 785282-Bromoethyl chloroformateHCID 86746207HCID 86746207, compound

Product 1

HCID 131717577HCID 131717577, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5.0 g (14.3 mmol) of 5-(cyanomethyl)-4-(2-methylpropyl)-2-(difluoromethyl)-6-(trifluoromethyl)-3-pyridinecarboxylic acid, methyl ester, prepared as in Example d, above, 8.02 g 2-bromoethyl chloroformate, and 0.3 g benzyltriethylammonium chloride in 125 mL dichloromethane was added 82 mL 50% NaOH. The solution was stirred at room temperature for one hour. The mixture was then poured into ice water and extracted twice with ethyl ether. The organic layer was washed with brine, dried over magnesium sulfate, filtered through silica gel, and concentrated to give 3.2 g of crude dark yellow oil. Chromatography using 50% ethyl acetate in hexanes yielded 2.0 g of the desired product as a light yellow oil, a 56% yield, which crystallized upon standing. m.p. 121°-122° C.

Workup

  1. extractionextracted twice with ethyl ether
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered through silica gel
  5. concentrationconcentrated
  6. customto give 3.2 g of crude dark yellow oil

Sources & evidence

ORD record
ord-950db0e79a914cb18bfe631f0bd32f12
Source dataset
uspto-grants-1992_10
Patent number
US05156670

Reaction notes

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