Chromone → Chromanone

HRID 1014774

반응식

HRID 1014774 반응식
[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

참가 물질

4

반응물 2

HCID 10286ChromoneHCID 81531Diisopropylethylamine

생성물 1

HCID 68110Chromanone수율 66%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-ee137c94384f44569122e528568b28cc
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07982064B2

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