Ethyl Acetate → HCID 18615107, compound

HRID 1636944Notes

Reaction equation

HRID 1636944 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=3[S:7][C:6]=2[CH:14]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:21]([O:28][C:29]([NH:31][CH2:32][CH2:33]Br)=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(OCC)(=O)C>CN(C)C=O.O>[CH2:21]([O:28][C:29]([NH:31][CH2:32][CH2:33][O:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=3[S:7][C:6]=2[CH:14]=1)=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 1501513-HydroxydibenzothiopheneHCID 278694benzyl N-(2-bromoethyl)carbamate

Product 1

HCID 18615107HCID 18615107, compoundYield 91.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 370.6 mg of 3-hydroxydibenzothiophene [prepared by the method reported by H. Kudo in J. Heterocycl. Chem., 22 (1), 215-218 (1985)] and 768 mg of potassium carbonate in 4 ml of dimethylformamide, 720 mg of Intermediate 0 were added and the mixture was heated at 60° C. for 30 hours. Thereto were added ethyl acetate and water to effect extraction, whereupon the organic layer was dried and the solvent was distilled off under a reduced pressure to thereby obtain 637 mg of the above-identified compound after purification by a column chromatography (mathanol/chloroform of 1/100). Rf=0.17 (ethyl acetate/n-hexane of 1/5).

Workup

  1. extractionextraction
  2. customwhereupon the organic layer was dried
  3. distillationthe solvent was distilled off under a reduced pressure

Sources & evidence

ORD record
ord-db81cf93b2ca43a7aa9a3ae8dd85d83e
Source dataset
uspto-grants-2000_03
Patent number
US06037362

Reaction notes

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