Potassium Iodide → HCID 86755265, compound

HRID 1637811Notes

Reaction equation

HRID 1637811 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C@H:13]([C:25]3[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33]Cl)=[CH:27][CH:26]=3)[C@H:14]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:15][O:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:35]([NH:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH2:36][CH2:37][CH3:38].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O.CO.C(Cl)Cl.O.CCOCC>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C@H:13]([C:25]3[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][N:39]([CH2:40][CH2:41][CH2:42][CH3:43])[CH2:35][CH2:36][CH2:37][CH3:38])=[CH:27][CH:26]=3)[C@H:14]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:15][O:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

9

Reactant 4

HCID 4875Potassium IodideHCID 8148DibutylamineHCID 11430Potassium CarbonateHCID 86755266HCID 86755266, compound

Product 1

HCID 86755265HCID 86755265, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

(+,-) cis 7-Benzyloxy-4-[4-(2-chloroethyloxy)-phenyl]-3-phenyl-chroman (235 mg, 0.5 mmol), N,N-dibutylamine (323 mg, 2.5 mmol), potassium carbonate (138 mg, 1 mmol) and potassium iodide (16 mg, 0.1 mmol) in dimethylformamide (5 ml) was stirred at 60° C. for 2 weeks. The reaction mixture was cooled and ether and water was added. The aqueous phase was extracted with ether, and the combined organic phases were washed with water and brine, dried (magnesium sulphate), and evaporated. The product was isolated by silica column chromatography using methanol-methylenechloride (1+19) as eluent.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionThe aqueous phase was extracted with ether
  3. washthe combined organic phases were washed with water and brine
  4. dry with materialdried (magnesium sulphate)
  5. customevaporated
  6. customThe product was isolated by silica column chromatography

Sources & evidence

ORD record
ord-944389f07cb34d3592951f923f1ba806
Source dataset
uspto-grants-2000_03
Patent number
US06043269

Reaction notes

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