Water → HCID 136128189, compound

HRID 1084659Notes

Reaction equation

HRID 1084659 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][CH:22]=[C:21]([S:25]([CH3:28])(=[O:27])=[O:26])[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:17]=[CH:16][C:15]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([S:25]([CH3:28])(=[O:27])=[O:26])[CH:20]=3)=[CH:14][CH:13]=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 178458874HCID 178458874, compound

Product 1

HCID 136128189HCID 136128189, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 1.8 g (4.3 mmol) of 2-propionyl-3-hydroxy-5-(4-(3-(methylsulfonyl)phenoxy)phenyl)-cyclohex-2-en-1-one in 5 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 0.50 g (6.1 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 thrice with 15 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 above named product as a pale oil in a yield of 1.8 g (91 percent of theoretical). 1H NMR (CDCl3): δ1.09-1.48 (m, 6H, both --CH2CH3 's), 2.57-3.60 (m includes s at 3.02 for CH3SO2 --, 10H), 4.13 (q, J=7 Hz, 2H, OCH2), 6.92-7.75 (m, 8H, aromatics), 14.9 (broad s, H, enol 1H) (Compound 3).

Workup

  1. extractionextracted thrice with 15 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 above named product as a pale oil in a yield of 1.8 g (91 percent of theoretical)

Sources & evidence

ORD record
ord-ffab80bf72be47a193cccaa7d07371a4
Source dataset
uspto-grants-1991_04
Patent number
US05006159

Reaction notes

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