Chromanone → Chroman
Reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]2[O:11][CH2:10][CH2:9][C:7](=O)[C:5]=2[CH:6]=1>CC(O)=O.[Zn]>[O:11]1[C:4]2[C:5](=[CH:6][CH:1]=[CH:2][CH:3]=2)[CH2:7][CH2:9][CH2:10]1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
Commercially available chromanone 11a (9.78 g, 66.0 mmol) dissolved in AcOH (20 mL) is added to a suspension of zinc dust (108 g, 1.65 mol) in AcOH (150 mL). The mixture is heated to 100° C. and is stirred mechanically overnight. The mixture is then filtered through Celite® (washed with EtOAc, 100 mL), diluted with PhMe (300 mL) and the solution is evaporated to give chroman intermediate 11b (8.45 g, 95% yield).
Workup
- filtrationThe mixture is then filtered through Celite® (washed with EtOAc, 100 mL)
- additiondiluted with PhMe (300 mL)
- customthe solution is evaporated
Sources & evidence
- ORD record
- ord-a2a3ac337fb547398da6fb3f41c5f4f4
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08377960B2
Reaction notes
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