Sodium Hydroxide → HCID 136209541, compound

HRID 1195459Notes

Reaction equation

HRID 1195459 reaction equation
Cl.[CH2:2]([O:4][NH2:5])[CH3:3].[OH-].[Na+].[OH:8][C:9]1[CH2:14][CH:13]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[CH2:20][CH2:19][CH2:18]3)[CH2:12][C:11](=[O:24])[C:10]=1[C:25](=O)[CH2:26][CH3:27]>C(O)C>[CH2:2]([O:4][N:5]=[C:25]([C:10]1[C:9](=[O:8])[CH2:14][CH:13]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[CH2:20][CH2:19][CH2:18]3)[CH2:12][C:11]=1[OH:24])[CH2:26][CH3:27])[CH3:3]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 76850O-ethylhydroxylamine hydrochlorideHCID 178458818HCID 178458818, compound

Product 1

HCID 136209541HCID 136209541, compoundYield 94.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethoxyamine hydrochloride (0.42 g; 4.1 mmole) and then aqueous 1% sodium hydroxide (17.0 ml) were added to a solution of 3-hydroxy-5-(5-indanyl)-2-propionylcyclohex-2-en-one (1.10 g; 3.87 mmole) in anhydrous absolute ethanol (200 ml). The mixture was stirred at room temperature for a period of 4 hours and then the ethanol was removed by evaporation under reduced pressure using a rotary evaporator. The residue was treated with dichloromethane and the organic phase was washed twice with dilute aqueous hydrochloric acid and twice with water. The organic phase was dried over anhydrous sodium sulphate and the solvent was removed by evaporation under reduced pressure to give the product, 2-[1-(ethoxyimino)propyl]-3-hydroxy-5-(5-indanyl)-cyclohex-2-en-1-one (1.20 g; 94.8%) as a pale yellow oil.

Workup

  1. customthe ethanol was removed by evaporation under reduced pressure
  2. customa rotary evaporator
  3. additionThe residue was treated with dichloromethane
  4. washthe organic phase was washed twice with dilute aqueous hydrochloric acid and twice with water
  5. dry with materialThe organic phase was dried over anhydrous sodium sulphate
  6. customthe solvent was removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-cf448421042b44b3b0a23f1cfa3fb3a7
Source dataset
uspto-grants-1992_05
Patent number
US05110989

Reaction notes

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