Methyl iodide → HCID 18957486, compound

HRID 2379573Notes

Reaction equation

HRID 2379573 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]3[CH2:19][CH2:18][CH:17]([OH:20])[CH:16]=3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[K+].I[CH3:24]>O>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]3[CH2:19][CH2:18][CH:17]([O:20][CH3:24])[CH:16]=3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 18957483HCID 18957483, compound

Product 1

HCID 18957486HCID 18957486, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-(3-Cyclopentyloxy-4-methoxyphenyl)-cyclopent-2-en-1-ol (150 mg, 0.55 mmol) (E10) was added to a suspension of powdered potassium hydroxide (89%, 138 mg, 2.2 mmol) under an argon atmosphere and then iodomethane (35μl, 0.56 mmol ) was added. The resulting mixture was stirred at room temperature for 3 hr, poured into water and extracted with ether. The ether extracts were washed three times with water, dried (sodium sulfate) and concentrated under reduced pressure. Purification by flash chromatography, eluting with 2:1 hexanes/ether, provided the title compound as an oil (120 mg, 76%).

Workup

  1. extractionextracted with ether
  2. washThe ether extracts were washed three times with water
  3. dry with materialdried (sodium sulfate)
  4. concentrationconcentrated under reduced pressure
  5. customPurification by flash chromatography
  6. washeluting with 2:1 hexanes/ether

Sources & evidence

ORD record
ord-5c32f1c46903445b943b700488a22449
Source dataset
uspto-grants-1994_11
Patent number
US05362915

Reaction notes

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