Potassium Carbonate → HCID 18625952, compound

HRID 1859950Notes

Reaction equation

HRID 1859950 reaction equation
Br[CH2:2][CH2:3][O:4][CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][O:6]1.C(=O)([O-])[O-].[K+].[K+].[OH:17][C:18]1[CH:39]=[CH:38][C:21]([CH2:22][CH:23]([CH2:29][CH2:30][O:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:20][CH:19]=1.CC(N(C)C)=O>CC(=O)CC>[O:31]([CH2:30][CH2:29][CH:23]([CH2:22][C:21]1[CH:38]=[CH:39][C:18]([O:17][CH2:2][CH2:3][O:4][CH:5]2[CH2:10][CH2:9][CH2:8][CH2:7][O:6]2)=[CH:19][CH:20]=1)[C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 31374DimethylacetamideHCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranHCID 18625752HCID 18625752, compound

Product 1

HCID 18625952HCID 18625952, compoundYield 84.6%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
100 °C

Procedure

2-(2-bromoethoxy)tetrahydropyran (1.24 g) and potassium carbonate (1.09 g) were added to a solution of ethyl 2-(4-hydroxybenzyl)-4-phenoxybutyrate (620 mg), which is the product of Reference example 3(d), in 2-butanone (8 ml). The mixture was stirred at 100° C. for 5 hours. To the reaction mixture dimethylacetamide (10 ml) was added and the mixture was stirred at 100° C. for 1.5 hours. At the end of this time the reaction mixture was partitioned between ethyl acetate and water. The ethyl acetate layer was separated and washed with saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate and then concentrated. The residue was purified via chromatography on a silica gel column using hexane/ethyl acetate=4/1 as the eluant to afford the desired compound (738 mg) as a syrup.

Workup

  1. stirringthe mixture was stirred at 100° C. for 1.5 hours
  2. customAt the end of this time the reaction mixture was partitioned between ethyl acetate and water
  3. customThe ethyl acetate layer was separated
  4. washwashed with saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified via chromatography on a silica gel column

Sources & evidence

ORD record
ord-3a0b61d79e2042f7a8a034ae8dadf75e
Source dataset
uspto-grants-2003_03
Patent number
US06528525B1

Reaction notes

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