Acetone → 7-(2-Iodoethyl)-1,2,3,4-tetramethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cycloheptene

HRID 2268494Notes

Reaction equation

HRID 2268494 reaction equation
CS(O[CH2:6][CH2:7][CH:8]1[CH2:14][CH2:13][C:12]2[C:15]([O:25][CH3:26])=[C:16]([O:23][CH3:24])[C:17]([O:21][CH3:22])=[C:18]([O:19][CH3:20])[C:11]=2[CH2:10][CH2:9]1)(=O)=O.[I-:27].[Na+].CC(C)=O>O>[I:27][CH2:6][CH2:7][CH:8]1[CH2:14][CH2:13][C:12]2[C:15]([O:25][CH3:26])=[C:16]([O:23][CH3:24])[C:17]([O:21][CH3:22])=[C:18]([O:19][CH3:20])[C:11]=2[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 180AcetoneHCID 5238Sodium IodideHCID 183485372-(1,2,3,4-tetramethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-7-yl)ethyl methanesulfonate

Product 1

HCID 183485187-(2-Iodoethyl)-1,2,3,4-tetramethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepteneYield 97.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The mixture of 2-(1,2,3,4-tetramethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-7-yl)ethyl methanesulfonate (3.12 g), sodium iodide (3.61 g), and acetone (40 ml) was heated under reflux for 1 hr. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with 5% aqueous sodium sulfite, water, and saturated aqueous sodium chloride, and dried. The solvent was removed in vacuo to yield the entitled compound (3.29 g) as crystals.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hr
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with 5% aqueous sodium sulfite, water, and saturated aqueous sodium chloride
  5. customdried
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-e85350e1f35645c7b581a0e872feca04
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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