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

HRID 2096500Notes

Reaction equation

HRID 2096500 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-8119ec8e82c44eeda0d2e3fbd36a1715
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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