O-(5-Chloro-thiophen-2-ylmethyl)-hydroxylamine → HCID 136058327, compound

HRID 1388639Notes

Reaction equation

HRID 1388639 reaction equation
[CH3:1][C:2]1([CH3:14])[CH2:7][C:6](=[O:8])[C:5]([C:9](=O)[CH2:10][CH3:11])=[C:4]([OH:13])[CH2:3]1.[Cl:15][C:16]1[S:20][C:19]([CH2:21][O:22][NH2:23])=[CH:18][CH:17]=1>C(O)C.C(Cl)Cl>[Cl:15][C:16]1[S:20][C:19]([CH2:21][O:22][N:23]=[C:9]([C:5]2[C:6](=[O:8])[CH2:7][C:2]([CH3:14])([CH3:1])[CH2:3][C:4]=2[OH:13])[CH2:10][CH3:11])=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 10986580O-(5-Chloro-thiophen-2-ylmethyl)-hydroxylamineHCID 178458888HCID 178458888, compound

Product 1

HCID 136058327HCID 136058327, compoundYield 70.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

In this example, a mixture containing 4.0 gms (0.02 mol) of 5,5-dimethyl-3-hydroxy-2-propionylcyclohex-2-en-1-one and 3.6 gms (0.022 mol) of O-[(5-chlorothien-2-yl)methyl]hydroxylamine in 75 mls of ethanol was stirred at room temperature for about 12 hours. The mixture was then evaporated to remove the ethanol, affording a thick syrup. The syrup was then dissolved in methylene chloride and extracted twice with aqueous 5% wt. sodium hydroxide. The aqueous layer was separated and acidified with concentrated hydrochloric acid and then extracted twice with methylene chloride. The methylene chloride layer was separated, dried with magnesium sulfate, and filtered. The filtrate was evaporated under vacuum, affording a viscous liquid which was then purified via column chromatography eluting with tetrahydrofuran-hexane (1:2 vol. ratio) affording 4.8 gms of 2-{1-[(5-chlorothien-2-ylmethoxy)imino]propyl}-3-hydroxy-5,5-dimethylcyclohex-2-en-1-one.

Workup

  1. customThe mixture was then evaporated
  2. customto remove the ethanol
  3. customaffording a thick syrup
  4. extractionextracted twice with aqueous 5% wt. sodium hydroxide
  5. customThe aqueous layer was separated
  6. extractionextracted twice with methylene chloride
  7. customThe methylene chloride layer was separated
  8. dry with materialdried with magnesium sulfate
  9. filtrationfiltered
  10. customThe filtrate was evaporated under vacuum
  11. customaffording a viscous liquid which
  12. customwas then purified via column chromatography
  13. washeluting with tetrahydrofuran-hexane (1:2 vol. ratio)

Sources & evidence

ORD record
ord-84f3d0cd6a2d4956baa05a57e0c35b48
Source dataset
uspto-grants-1984_02
Patent number
US04432786

Reaction notes

Loading…