Chromone → Chromanone

HRID 1014774Notes

Reaction equation

HRID 1014774 reaction equation
[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[CH:3]=[CH:2]1.CCN(C(C)C)C(C)C>C1(C)C=CC=CC=1>[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 10286ChromoneHCID 81531Diisopropylethylamine

Product 1

HCID 68110ChromanoneYield 66%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

According to the general procedure, a solution of chromone (45 mg, 0.31 mmol), Hünig's base (540 μL) and rac-32 (9.8 mg, 0.0062 mmol, 2.0 mol %) in PhMe (3 mL) was pressurized with H2 to 100 bar and stirred for 48 h. Filtration of the reaction mixture and evaporation of the solvent gave the crude product, which was purified by column chromatography (30% EtOAc in hexane, silica gel) to give 48 (30 mg, 66%) as a colorless oil. 1H NMR35 (300 MHz, CDCl3): δ 7.90 (dd, 1H J=7.8, 1.5 Hz), 7.50-7.45 (m, 1H), 7.05-6.96 (m, 2H), 4.54 (t, 2H, J=6.6 Hz), 2.82 (t, 2H, J=6.3 Hz); 13C NMR (75.5 MHz, CDCl3): δ 192.0, 162.0, 136.1, 127.3, 121.5, 118.0, 67.1, 37.9.

Workup

  1. filtrationFiltration of the reaction mixture and evaporation of the solvent
  2. customgave the crude product, which
  3. customwas purified by column chromatography (30% EtOAc in hexane, silica gel)

Sources & evidence

ORD record
ord-ee137c94384f44569122e528568b28cc
Source dataset
uspto-grants-2011_07
Patent number
US07982064B2

Reaction notes

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