Water → HCID 136144744, compound

HRID 1084661Notes

Reaction equation

HRID 1084661 reaction equation
[C:1]([C:5]1[C:6](=[O:30])[CH2:7][CH:8]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]3[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=O)=O)=[CH:21][C:20]=3[F:29])[CH:13]=2)[CH2:9][C:10]=1[OH:11])(=O)[CH2:2][CH3:3].Cl.[CH2:32]([O:34][NH2:35])[CH3:33].C([O-])(=O)C.[Na+].O>C(Cl)Cl.C(O)C>[CH2:32]([O:34][N:35]=[C:1]([C:5]1[C:10](=[O:11])[CH2:9][CH:8]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]3[CH:24]=[CH:23][C:22]([S:25][CH3:28])=[CH:21][C:20]=3[F:29])[CH:13]=2)[CH2:7][C:6]=1[OH:30])[CH2:2][CH3:3])[CH3:33]

Participants

7

Reactant 4

HCID 962WaterHCID 76850O-ethylhydroxylamine hydrochlorideHCID 517045Sodium AcetateHCID 178458859HCID 178458859, compound

Product 1

HCID 136144744HCID 136144744, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 0.70 g (1.8 mmol) of 2-propionyl-3-hydroxy-5-(3-(2-fluoro-4-(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 0.22 g (2.3 mmol) of ethoxyamine hydrochloride and 0.19 g (2.3 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 30 mL portions of methylene chloride. The combined extracts were dried over MgSO4, filtered and the solvent evaporated off leaving the product as a dark yellow oil. Purification via flash chromatography (silica gel, methylene chloride/hexane) the above named product as a light amber oil in a yield of 0.6 g (77 percent of theoretical). 1H NMR (CDCl3): δ1.2-1.5 (m, 6H, both --CH2CH3 's), 2.58 (s, 3H, --SCH3), 2.50-3.65 (m, 7H), 4.25 (q, J=7 Hz, 2H, --OCH2), 6.8-7.5 (m, 7H, aromatics), 14.9 (broad s, 1H, enol H) (Compound 5).

Workup

  1. extractionextracted twice with 30 mL portions of methylene chloride
  2. dry with materialThe combined extracts were dried over MgSO4
  3. filtrationfiltered
  4. customthe solvent evaporated off

Sources & evidence

ORD record
ord-b888de09439c4cc2b9628e2042ca25c9
Source dataset
uspto-grants-1991_04
Patent number
US05006159

Reaction notes

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