Potassium Carbonate → HCID 11339601, compound

HRID 1108067Notes

Reaction equation

HRID 1108067 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:19])[CH:5]=[C:6]([C:8]2([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:7]=1.Cl.[CH3:21][C:22]1[N:23]([C:27]2[CH:34]=[CH:33][C:30]([CH2:31]Cl)=[CH:29][CH:28]=2)[CH:24]=[CH:25][N:26]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C.C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([O:19][CH2:31][C:30]2[CH:29]=[CH:28][C:27]([N:23]3[CH:24]=[CH:25][N:26]=[C:22]3[CH3:21])=[CH:34][CH:33]=2)[CH:5]=[C:6]([C:8]2([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)[CH:7]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 187863424-(2-Methylimidazol-1-yl)benzyl chloride hydrochlorideHCID 187863744-(3-Fluoro-5-hydroxyphenyl)-3,4,5,6-tetrahydro-2H-pyran-4-carboxylate Ethyl

Product 1

HCID 11339601HCID 11339601, compoundYield 68%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A stirred mixture of ethyl 4-(5-fluoro-3-hydroxyphenyl)-3,4,5,6-tetrahydro-2H-pyran-4-carboxylate (2.01 g, 7.5 mmol), 4-(2-methylimidazol-1-yl)benzyl chloride hydrocloride (1.82 g, 7.5 mmol) and potassium carbonate (5.18 g, 37.5 mmol) in DMF (30 ml) was heated at 100° C. for 1.33 hr. After cooling to room temperature, the mixture was diluted with a mixture of ethyl acetate and toluene (2:1, 200 ml), and washed with water (4×100 ml) and brine (100 ml), dried (magnesium sulfate) and concentrated to give 3.38 g of crude product as amber solids. Recrystallization from a mixture of isopropyl ether (25 ml) and ethyl acetate (2 ml) gave the titled compound (2.22 g, 68%).

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed with water (4×100 ml) and brine (100 ml)
  3. dry with materialdried (magnesium sulfate)
  4. concentrationconcentrated
  5. customto give 3.38 g of crude product as amber solids
  6. customRecrystallization
  7. additionfrom a mixture of isopropyl ether (25 ml) and ethyl acetate (2 ml)

Sources & evidence

ORD record
ord-e914be253ae74651ba5a198c73cbbf7b
Source dataset
uspto-grants-2000_05
Patent number
US06063928

Reaction notes

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