5'-Bromo-2'-hydroxyacetophenone → 6-bromo-2-(tetrahydro-2H-pyran-3-yl)chroman-4-one

HRID 1408688Notes

Reaction equation

HRID 1408688 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.[O:12]1[CH2:17][CH2:16][CH2:15][CH:14]([CH:18]=O)[CH2:13]1>C(O)C.O>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[O:11][CH:18]([CH:14]1[CH2:15][CH2:16][CH2:17][O:12][CH2:13]1)[CH2:9][C:8]2=[O:10]

Participants

5

Reactant 2

HCID 959915'-Bromo-2'-hydroxyacetophenoneHCID 10129928Oxane-3-carbaldehyde

Product 1

HCID 584241476-bromo-2-(tetrahydro-2H-pyran-3-yl)chroman-4-oneYield 20%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A mixture of 1-(5-bromo-2-hydroxyphenyl)ethanone (39 g, 181.8 mmol), tetrahydro-2H-pyran-3-carbaldehyde (20 g, 181.8 mmol) and borax (69.3 g, 181.8 mmol) in ethanol (240 mL) and H2O (400 mL) was refluxed for one day. The reaction mixture was cooled, diluted with an equal volume of H2O and extracted with ethyl acetate. The organic layer was dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to give 6-bromo-2-(tetrahydro-2H-pyran-3-yl)chroman-4-one (10 g, 20%).

Workup

  1. temperaturewas refluxed for one day
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2fb87bf457da4e13973f024e09ca42e9
Source dataset
uspto-grants-2014_12
Patent number
US08921359B2

Reaction notes

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