Ethanol → HCID 21289577, compound

HRID 867990Notes

Reaction equation

HRID 867990 reaction equation
[O:1]=[C:2]([CH3:23])[CH2:3][CH2:4][C:5]1([CH2:20][CH2:21][CH3:22])[CH2:14][CH2:13][C:12]2[C:7](=[C:8]([Cl:18])[C:9]([Cl:17])=[C:10]([O:15][CH3:16])[CH:11]=2)[C:6]1=O.C(O)C.[OH-].[Na+]>O>[Cl:17][C:9]1[C:10]([O:15][CH3:16])=[CH:11][C:12]2[CH2:13][CH2:14][C:5]3([CH2:20][CH2:21][CH3:22])[C:6]([C:7]=2[C:8]=1[Cl:18])=[CH:23][C:2](=[O:1])[CH2:3][CH2:4]3

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 14257706HCID 14257706, compound

Product 1

HCID 21289577HCID 21289577, compoundYield 52.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-(3-Oxobutyl)-7,8-dichloro-6-methoxy-2-propyl-1-tetralone (700 mg), ethanol (25 ml), water (6 ml) and 10N sodium hydroxide solution (200 μl) were combined and stirred at room temperature for 96 hours. The reaction mixture was evaporated in vacuo at 30° C. treated with water, extracted two times with 100 ml of ether, washed with water, brine dried over MgSO4, evaporated in vacuo, and chromatographed on 25 g of SiO2 (ethyl acetate-hexane; 1:2) to give 350 mg of 3,4-Dichloro-6,7,8,8a,9,10-hexahydro-2-methoxy-6-oxo-8a-propylphenanthrene which was used in the next step.

Workup

  1. customThe reaction mixture was evaporated in vacuo at 30° C.
  2. additiontreated with water
  3. extractionextracted two times with 100 ml of ether
  4. washwashed with water, brine
  5. dry with materialdried over MgSO4
  6. customevaporated in vacuo
  7. customchromatographed on 25 g of SiO2 (ethyl acetate-hexane; 1:2)

Sources & evidence

ORD record
ord-f3adfff5489345a38a5b37dd4046268f
Source dataset
uspto-grants-1988_10
Patent number
US04777281

Reaction notes

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