Water → HCID 136053482, compound

HRID 1084658Notes

Reaction equation

HRID 1084658 reaction equation
[C:1]([C:5]1[C:6](=[O:29])[CH2:7][CH:8]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([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: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][CH:15]=[C:14]([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: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 178458854HCID 178458854, compound

Product 1

HCID 136053482HCID 136053482, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 3.5 g (8.5 mmol) of 2-propionyl-3-hydroxy-5-(3-(3-(methylsulfonyl)phenoxy)phenyl)-cyclohex-2-en-1-one in 10 mL of methylene chloride and 20 mL of absolute ethanol was treated with 1.0 g (1.0 mmol) of ethoxyamine hydrochloride and 0.9 g (1.0 mmol) of anhydrous sodium acetate. After stirring for 24 hours, the mixture was poured into 100 mL of water and extracted thrice with 20 mL portions of methylene chloride. The combined extracts were dried over MgSO4, filtered and passed through a short column of silica gel, eluting with about 200 mL of methylene chloride. Evaporation of the eluent afforded the above named product as a light yellow oil. The product was recovered in a yield of 3.0 g (77 percent of theoretical). 1H NMR (CDCl3) δ1.08-1.49 (m, 6H, both --CH2CH3 's), 2.60-3.65 (m includes s at 3.05 for CH3SO2 --, 10H), 4.12 (q, J=7Hz, 2H, --OCH2), 6.85-7.85 (m, 8H, aromatics), 14.9 (broad s, 1H, enol H) (Compound 1).

Workup

  1. extractionextracted thrice with 20 mL portions of methylene chloride
  2. dry with materialThe combined extracts were dried over MgSO4
  3. filtrationfiltered
  4. washeluting with about 200 mL of methylene chloride
  5. customEvaporation of the eluent
  6. customafforded the above named product as a light yellow oil
  7. customThe product was recovered in a yield of 3.0 g (77 percent of theoretical)

Sources & evidence

ORD record
ord-f9089e26497e4e2fa6a5e7117aeafe6d
Source dataset
uspto-grants-1991_04
Patent number
US05006159

Reaction notes

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