Pyridine → HCID 21286119, compound

HRID 2231150Notes

Reaction equation

HRID 2231150 reaction equation
[CH3:1][C:2]1([CH3:11])[CH2:7][C:6](=[O:8])[CH2:5][C:4](=[O:9])[CH:3]1[F:10].N1C=CC=CC=1.[N+:18]([C:21]1[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[CH:26][C:22]=1[C:23](Cl)=[O:24])([O-:20])=[O:19]>C(Cl)Cl>[CH3:1][C:2]1([CH3:11])[CH:3]([F:10])[C:4](=[O:9])[CH:5]=[C:6]([O:8][C:23](=[O:24])[C:22]2[CH:26]=[CH:27][C:28]([C:30]([F:33])([F:32])[F:31])=[CH:29][C:21]=2[N+:18]([O-:20])=[O:19])[CH2:7]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 143235242-Nitro-4-(trifluoromethyl)benzoyl chlorideHCID 14326953HCID 14326953, compound

Product 1

HCID 21286119HCID 21286119, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5,5-Dimethyl-4-fluoro-1,3-cyclohexanedione [0.5 grams (g), 0.0032 mole, prepared according to the teaching of Liebigs Ann. Chem., 679, 9 (1964)] and 0.25 g (0.0032 mole) pyridine were dissolved in 20 milliliters (ml) methylene chloride at room temperature. 2-Nitro-4-trifluoromethylbenzoyl chloride (1.0 g, 0.0039 mole) dissolved in 20 ml methylene chloride was slowly added with cooling. The reaction mixture was stirred at room temperature for 24 hours and then washed two times with water, one time with saturated sodium bicarbonate aqueous solution and one with with water. The aqueous phases were discarded and the organic phase dried with MgSO4 and then evaporated to yield the intermediate enol ester, 5,5-dimethyl-6-fluoro-3-(2-nitro-4-trifluoromethylbenzoyloxy)cyclohex-2-enone. The 5,5-dimethyl-6-fluoro-3-(2-nitro-4-trifluoromethylbenzoyloxy)cyclohex-2-enone was dissolved in 30 ml acetonitrile and triethylamine (0.7 g, 0.007 mole) which was added all at once, followed by acetonecyanohydrin (0.05 g, 0.0006 mole). The solution was stirred for 24 hours. The solvent was evaporated and the residue washed with diethyl ether to yield the product.

Workup

  1. additionwas slowly added
  2. temperaturewith cooling
  3. washwashed two times with water, one time with saturated sodium bicarbonate aqueous solution and one with with water
  4. dry with materialthe organic phase dried with MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-7119eeb9982d496a8ab497d5e806b598
Source dataset
uspto-grants-1988_11
Patent number
US04781751

Reaction notes

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