Triethylamine → HCID 178499206, compound

HRID 1838634Notes

Reaction equation

HRID 1838634 reaction equation
[CH3:1][C:2]1[N:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[OH:15][C:16]1[C:17]([O:28][CH3:29])([C:24]([O:26][CH3:27])=[O:25])[CH2:18][CH:19]([CH3:23])[C:20](=[O:22])[CH:21]=1.C(N(CC)CC)C.[C-]#N.[K+]>C(#N)C>[OH:15][C:16]1[C:17]([O:28][CH3:29])([C:24]([O:26][CH3:27])=[O:25])[CH2:18][CH:19]([CH3:23])[C:20](=[O:22])[C:21]=1[C:4]([C:3]1[C:2]([CH3:1])=[N:10][C:9]([C:11]([F:14])([F:13])[F:12])=[CH:8][CH:7]=1)=[O:5]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9032Potassium CyanideHCID 27756752-Methyl-6-(trifluoromethyl)nicotinoyl chlorideHCID 18755506Methyl 2-hydroxy-1-methoxy-5-methyl-4-oxocyclohex-2-enecarboxylate

Product 1

HCID 178499206HCID 178499206, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2.23 g of fresh 2-methyl-6-trifluoromethyinicotinoyl chloride are added to a mixture of 2.14 g of methyl 2-hydroxy-1-methoxy-5-methyl-4-oxocyclohex-2-enecarboxylate and 2.02 g of triethylamine in 30 ml of acetonitrile. After approximately 30 minutes, 0.065 g of potassium cyanide is added and the mixture is stirred for 18 hours. At pH 2, the mixture is subsequently partitioned between water and ethyl acetate, dried over magnesium sulfate and evaporated. Filtration on silica gel (mobile phase ethyl acetate/methanol/triethylamine 85:10:5) gives the pure methyl 2-hydroxy-1-methoxy-5-methyl-3-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)-4-oxocyclohex-2-enecarboxylate as a viscous oil.

Workup

  1. customAt pH 2, the mixture is subsequently partitioned between water and ethyl acetate
  2. dry with materialdried over magnesium sulfate
  3. customevaporated
  4. filtrationFiltration on silica gel (mobile phase ethyl acetate/methanol/triethylamine 85:10:5)

Sources & evidence

ORD record
ord-a0dee3e592614648a3cb62ce71889d5c
Source dataset
uspto-grants-2004_01
Patent number
US06673938B1

Reaction notes

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