Sodium Hydroxide → HCID 86746206, compound

HRID 466473Notes

Reaction equation

HRID 466473 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].Br[CH2:26][CH2:27][CH2:28][C:29](Cl)=[O:30].[OH-].[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.ClCCl>[C:1]([C:3](=[C:29]1[CH2:28][CH2:27][CH2:26][O:30]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

6

Reactant 3

HCID 14798Sodium HydroxideHCID 702254-Bromobutyryl chloride2×HCID 86746207HCID 86746207, compound

Product 1

HCID 86746206HCID 86746206, compoundYield 24%

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, 6.62 g (35.7 mmol) of 4-bromobutyryl chloride and 0.37 g of benzyltriethylammonium chloride in 160 mL dichloromethane was added 82 mL 50% NaOH. The solution turned red and was stirred for 15 min. Stirring was interrupted due to viscosity of solution; 0.5 mL additional 4-bromobutyryl chloride was added to enable stirring. The solution was poured into 175 mL of ice water and extracted with ethyl ether. The organic layer was washed with water, brine, and dried over magnesium sulfate. The solution was filtered through silica gel to give 5.8 g of the crude product as a dark red oil. Purification by chromatography using 30% ethyl acetate in hexanes yielded 1.4 g of the desired product as an oil, a 24% yield. nD25 1.4882.

Workup

  1. stirringStirring
  2. stirringto enable stirring
  3. extractionextracted with ethyl ether
  4. washThe organic layer was washed with water, brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationThe solution was filtered through silica gel
  7. customto give 5.8 g of the crude product as a dark red oil
  8. customPurification by chromatography

Sources & evidence

ORD record
ord-ff76baa670304bb9ac66e7ffea0c0347
Source dataset
uspto-grants-1992_10
Patent number
US05156670

Reaction notes

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