Iodoethane → HCID 22490930, compound

HRID 2180598Notes

Reaction equation

HRID 2180598 reaction equation
[Br:1][C:2]1[C:11]2[C:10]([CH3:13])([CH3:12])[CH2:9][CH:8]=[C:7]([CH:14]([CH3:16])[CH3:15])[C:6]=2[CH:5]=[C:4]([C:17](=[O:19])[CH3:18])[C:3]=1[OH:20].C(=O)([O-])[O-].[K+].[K+].[CH2:27](I)[CH3:28]>CC(C)=O.O>[Br:1][C:2]1[C:11]2[C:10]([CH3:13])([CH3:12])[CH2:9][CH:8]=[C:7]([CH:14]([CH3:16])[CH3:15])[C:6]=2[CH:5]=[C:4]([C:17](=[O:19])[CH3:18])[C:3]=1[O:20][CH2:27][CH3:28]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 22490824HCID 22490824, compound

Product 1

HCID 22490930HCID 22490930, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A mixture of 1-(4-bromo-3-hydroxy-8-isopropyl-5,5-dimethyl-5,6-dihydro-naphthalen-2-yl)-ethanone (Compound A-106, 1.61 g, 4.77 mmol), potassium carbonate (1.97 g, 14.31 mmol) and ethyl iodide (3.8 mL, 47.7 mmol) in acetone (50 mL) was heated to reflux for 16 h. The reaction mixture was cooled to room temperature, diluted with water and extracted with diethyl ether. The combined ethereal layers were washed with water, brine, dried (Na2SO4), filtered and concentrated in vacuo to give the title compound as a yellow oil. The material was used in the next step without further purification.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 16 h
  3. extractionextracted with diethyl ether
  4. washThe combined ethereal layers were washed with water, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e36bccdb2ee3477bb6b30a953db54f02
Source dataset
uspto-grants-2005_05
Patent number
US06887896B1

Reaction notes

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