Water → HCID 136027398, compound

HRID 1084660Notes

Reaction equation

HRID 1084660 reaction equation
[C:1]([C:5]1[C:6](=[O:29])[CH2:7][CH:8]([C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]3[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=3)=[CH:14][CH:13]=2)[CH2:9][C:10]=1[OH:11])(=O)[CH2:2][CH3:3].Cl.[CH2:31]([O:33][NH2:34])[CH3:32].C([O-])(=O)C.[Na+].O>C(Cl)Cl.C(O)C>[CH2:31]([O:33][N:34]=[C:1]([C:5]1[C:6](=[O:29])[CH2:7][CH:8]([C:12]2[CH:13]=[CH:14][C:15]([O:18][C:19]3[CH:20]=[CH:21][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:23][CH:24]=3)=[CH:16][CH:17]=2)[CH2:9][C:10]=1[OH:11])[CH2:2][CH3:3])[CH3:32]

Participants

7

Reactant 4

HCID 962WaterHCID 76850O-ethylhydroxylamine hydrochlorideHCID 517045Sodium AcetateHCID 178458875HCID 178458875, compound

Product 1

HCID 136027398HCID 136027398, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 1.6 g (3.9 mmol) of 2-propionyl-3-hydroxy-5-(4-(4-(methylsulfonyl)phenoxy)phenyl)-cyclohex-2-en-1-one in 10 mL of methylene chloride and 10 mL of absolute ethanol, at room temperature was treated with 0.50 g (5.2 mmol)of ethoxyamine hydrochloride and 0.40 g (4.9 mmol) of anhydrous sodium acetate. After stirring under a nitrogen atmosphere for 16 hours, the mixture was poured into 100 mL of water and extracted twice with 20 mL portions of methylene chloride. The combined extracts were dried over MgSO4, filtered and passed through a short column of silica gel. Evaporation of the solvent left the product as a solid residue which was recrystallized from a mixture of diethyl ether and methylene chloride to yield 1.5 g (84 percent of theoretical) the above named product as a white solid melting at 155°-157° C. 1H NMR (CDCl3): δ1.10-1.48 (m, 6H, both --CH2CH3 's), 2.57-3.62 (m includes s at 3.03 for CH3SO2 --, 10H), 4.12 (q, J=7 Hz, 2H, --OCH2), 6.95-7.45 (m, 6H, aromatics), 7.90 (d, J=7 Hz, 2H, aromatics), 15.0 (very broad s, enol H) (Compound 4).

Workup

  1. extractionextracted twice with 20 mL portions of methylene chloride
  2. dry with materialThe combined extracts were dried over MgSO4
  3. filtrationfiltered
  4. customEvaporation of the solvent
  5. waitleft the product as a solid residue which
  6. customwas recrystallized from a mixture of diethyl ether and methylene chloride

Sources & evidence

ORD record
ord-f846b155b4ac4f748d87a31781bff471
Source dataset
uspto-grants-1991_04
Patent number
US05006159

Reaction notes

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