Chromanone → Chroman

HRID 590980Notes

Reaction equation

HRID 590980 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>C(O)(=O)C.[Zn]>[O:11]1[C:4]2[CH:3]=[CH:2][CH:1]=[CH:6][C:5]=2[CH2:7][CH2:9][CH2:10]1

Participants

4

Reactant 1

HCID 68110Chromanone

Product 1

HCID 136319Chroman

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of chromanone (1 g, 6.75 mmol) and zinc powder (3.07 g, 47 mmol) in acetic acid (15 mL) was warmed at 100° C. for 15 hours. Residue of zinc was then removed by filtration on Celite®. The filtrate was concentrated under vacuum by co-evaporation with toluene to give the desired product (9a) without further purification (810 mg, 6.03 mmol, 89%).

Workup

  1. customResidue of zinc was then removed by filtration on Celite®
  2. concentrationThe filtrate was concentrated under vacuum by co-evaporation with toluene

Sources & evidence

ORD record
ord-1a786bee5b664105b28c3ff4fa86ffa5
Source dataset
uspto-grants-2016_01
Patent number
US09238026B2

Reaction notes

Loading…