Chromone → Chromanone

HRID 1014774

反応式

HRID 1014774 の反応式
[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

参加物

4

反応物 2

HCID 10286ChromoneHCID 81531Diisopropylethylamine

生成物 1

HCID 68110Chromanone収率 66%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-ee137c94384f44569122e528568b28cc
出典データセット
uspto-grants-2011_07
特許番号
US07982064B2

関連ノート

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