Hydrochloric Acid → HCID 23036990, compound

HRID 1709090Notes

Reaction equation

HRID 1709090 reaction equation
[Na].[CH:2]([C:5]1[CH:9]=[C:8]([CH:10]2[CH2:15][C:14](=[O:16])[CH2:13][C:12](=[O:17])[CH:11]2[C:18]([O:20][CH3:21])=[O:19])[O:7][N:6]=1)([CH3:4])[CH3:3].[C:22](Cl)(=[O:26])[CH2:23][CH2:24][CH3:25].Cl>O1CCCC1.C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:22]([C:13]1[C:14](=[O:16])[CH2:15][CH:10]([C:8]2[O:7][N:6]=[C:5]([CH:2]([CH3:4])[CH3:3])[CH:9]=2)[CH:11]([C:18]([O:20][CH3:21])=[O:19])[C:12]=1[OH:17])(=[O:26])[CH2:23][CH2:24][CH3:25]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8855Butyryl chlorideHCID 5360545SodiumHCID 23036987HCID 23036987, compound

Product 1

HCID 23036990HCID 23036990, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

15.1 g of the sodium salt of 5-(3-isopropylisoxazol-5-yl)-4-methoxycarbonylcyclohexane-1,3-dione was suspended in 150 ml of tetrahydrofuran; 6.4 g butyryl chloride was added while cooling with ice. After the mixture had been stirred for 15 hours it was filtered and concentrated. The residue obtained was taken up in methylene chloride, 2 g of 4-(N,N-dimethylamino)-pyridine was added, and the mixture was stirred for 3 days. After shaking with 10 wt % hydrochloric acid and then with water, the mixture was dried over sodium sulfate and concentrated. 15 g of 2-butyryl-3-hydroxy-5(3-isopropylisoxazol-5-yl)-4-methoxycarbonylcyclohex-2-en-1-one was obtained as an isomer mixture, and was then stirred with 300 ml of 10 wt % strength sodium hydroxide solution at 25° C. for 16 hours. The pH of the solution was then adjusted to 2 concentrated hydrochloride acid, and stirring was carried out for 2 hours at 85° C. After cooling the product was filtered off, washed with water and recrystallized from isopropanol. There was obtained 2-butyryl-3-hydroxy-5(3-isopropylisoxazol-5-yl)-cyclohex-2-en-1-one of m.p. 105°-107° C. (compound no. 64).

Workup

  1. temperaturewhile cooling with ice
  2. filtrationwas filtered
  3. concentrationconcentrated
  4. customThe residue obtained
  5. stirringthe mixture was stirred for 3 days
  6. dry with materialwith water, the mixture was dried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-40cdecda4d574cb0921907f7873ce596
Source dataset
uspto-grants-1990_08
Patent number
US04948415

Reaction notes

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