Ethyl Acetate → HCID 21834061, compound

HRID 1956931Notes

Reaction equation

HRID 1956931 reaction equation
Br[CH2:2][CH2:3][O:4][CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][O:6]1.[OH:11][N:12]1[C:16](=[O:17])[C:15]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]2[C:13]1=[O:22].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O.O>[O:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH:5]1[O:4][CH2:3][CH2:2][O:11][N:12]1[C:13](=[O:22])[C:14]2=[CH:21][CH:20]=[CH:19][CH:18]=[C:15]2[C:16]1=[O:17]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10665N-HydroxyphthalimideHCID 11430Potassium CarbonateHCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyran

Product 1

HCID 21834061HCID 21834061, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 10.8 g of 2-(2-bromoethoxy)tetrahydropyran, 7.0 g of N-hydroxyphthalimide and 11.1 g of potassium carbonate in 100 ml of dimethylformamide was stirred at 80° C. for 2.5 hours. Ethyl acetate and water were then added to the reaction mixture to make a solution. The ethyl acetate layer was then separated and dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure, after which the resulting residue was purified by column chromatography through silica gel, using a 2:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 8.62 g of the title compound as a syrup.

Workup

  1. customThe ethyl acetate layer was then separated
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was then removed by distillation under reduced pressure
  4. customafter which the resulting residue was purified by column chromatography through silica gel
  5. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-f0d8f87eedbd40d88c178065f775b07f
Source dataset
uspto-grants-1998_07
Patent number
US05780490

Reaction notes

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