Hexanoyl chloride → HCID 13912741, compound

HRID 2118415Notes

Reaction equation

HRID 2118415 reaction equation
[K].[CH3:2][CH:3]([CH:5]1[CH2:10][C:9](=[O:11])[CH:8]([C:12]2[C:17]([CH3:18])=[N:16][C:15]([CH3:19])=[C:14]([CH3:20])[N:13]=2)[C:7](=[O:21])[CH2:6]1)[CH3:4].[C:22](Cl)(=[O:28])[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]>C(OCC)(=O)C.CCCCCC>[C:22]([O:21][C:7]1[CH2:6][CH:5]([CH:3]([CH3:2])[CH3:4])[CH2:10][C:9](=[O:11])[C:8]=1[C:12]1[C:17]([CH3:18])=[N:16][C:15]([CH3:19])=[C:14]([CH3:20])[N:13]=1)(=[O:28])[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

4

Reactant 2

HCID 67340Hexanoyl chlorideHCID 70431917HCID 70431917, compound

Product 1

HCID 13912741HCID 13912741, compound

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

The subject compound was prepared by reaction of 5-(1-methylethyl)-2-(3,5,6-trimethyl-2-pyrazinyl)-1,3-cyclohexanedione potassium salt (Example 8) with hexanoyl chloride employing the general procedure described in Example 3, but allowing the reaction mixture to stir at room temperature over the weekend. Following the reaction, the ether solution of crude product was extracted quickly with ice-cold 0.25N NaOH, dried (MgSO4), filtered and evaporated to give a residue product showing some acid chloride contamination by IR examination. Dry-column chromatography using 1:1 ethyl acetate/hexane gave analytically pure material as shown by the elemental analysis of Table II.

Workup

  1. customthe reaction
  2. extractionthe ether solution of crude product was extracted quickly with ice-cold 0.25N NaOH
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customto give a residue product
  7. customgave analytically pure material

Sources & evidence

ORD record
ord-3c4e68c39c7e40ea8c15f66945e4c1d8
Source dataset
uspto-grants-1987_07
Patent number
US04678501

Reaction notes

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