Potassium Carbonate → HCID 24697475, compound

HRID 1891004Notes

Reaction equation

HRID 1891004 reaction equation
[C:1]([O-:4])([O-])=O.[K+].[K+].O[CH2:8][C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:10].BrC[CH:19]1[CH2:23][CH2:22][CH2:21][O:20]1>CN(C=O)C.O>[O:20]1[CH2:21][CH2:22][CH2:23][CH:19]1[CH2:1][O:4][C:16]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:9](=[O:10])[CH3:8]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 14501Furan, 2-(bromomethyl)tetrahydro-HCID 68490alpha-Hydroxyacetophenone

Product 1

HCID 24697475HCID 24697475, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

K2CO3 (4.5 g, 0.032 mol) was added to a solution of 2-hydroxy-acetophenone (4 g, 0.03 mol) and 2-bromomethyl-tetrahydro-furan (10 g, 0.06 mol) in DMF (20 mL). The resulting mixture was vigorously stirred for 16 h at 110° C., cooled and then diluted with water (100 mL), extracted with EtOAc (3×50 mL). The combined organic layers were washed with water (2×30 mL), filtered over anhydrous Na2SO4, filtered and the solvent removed under reduced pressure. The crude product was purified by flash chropatography on silica gel (eluent EtOAc-hexane, 1:5) to give 1-[2-(tetrahydro-furan-2-ylmethoxy)-phenyl]-ethanone (2.22 g; 34%) as brown oil.

Workup

  1. temperaturecooled
  2. extractionextracted with EtOAc (3×50 mL)
  3. washThe combined organic layers were washed with water (2×30 mL)
  4. filtrationfiltered over anhydrous Na2SO4
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure
  7. customThe crude product was purified by flash chropatography on silica gel (eluent EtOAc-hexane, 1:5)

Sources & evidence

ORD record
ord-e8ebcc9800c94a42b3ec897667670ec0
Source dataset
uspto-grants-2013_08
Patent number
US08507498B2

Reaction notes

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