Hydrochloric Acid → HCID 136393657, compound

HRID 978319Notes

Reaction equation

HRID 978319 reaction equation
[OH:1][C:2]1[CH2:7][CH:6]([C:8]2[O:12][C:11]3[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=3[CH:9]=2)[CH2:5][C:4](=[O:17])[C:3]=1[C:18](=O)[CH2:19][CH2:20][CH3:21].Cl.[CH2:24]([O:26][NH2:27])[CH3:25].C([O-])(=O)C.[Na+].Cl>C(O)C>[CH2:24]([O:26][N:27]=[C:18]([C:3]1[C:4](=[O:17])[CH2:5][CH:6]([C:8]2[O:12][C:11]3[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=3[CH:9]=2)[CH2:7][C:2]=1[OH:1])[CH2:19][CH2:20][CH3:21])[CH3:25]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 76850O-ethylhydroxylamine hydrochlorideHCID 517045Sodium AcetateHCID 178450306HCID 178450306, compound

Product 1

HCID 136393657HCID 136393657, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-hydroxy-5-(benzo[b]furan-2-yl)-2-butyryl cyclohex-2-en-1-one (1.0 g), ethoxyamine hydrochloride (0.36 g), sodium acetate (0.3 g) and ethanol (100 ml) were stirred at room temperature for 12 hr. The mixture was poured into a very dilute aqueous hydrochloric acid solution which was then extracted with ether. Evaporation of the dried (MgSO4) organic fraction and purification of the residue by column chromatography over silica with dichloromethane elution gave 2-[1-(ethoxyimino)butyl]-3-hydroxy-5-(benzo[b]furan-2-yl)cyclohex-2-en-1-one as a yellow solid, mp 70° C.

Workup

  1. extractionwas then extracted with ether
  2. customEvaporation of the
  3. customdried
  4. custom(MgSO4) organic fraction and purification of the residue by column chromatography over silica
  5. washwith dichloromethane elution

Sources & evidence

ORD record
ord-0e1ab3cf1581461abd10fcae4530e6c4
Source dataset
uspto-grants-1987_05
Patent number
US04664693

Reaction notes

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