Benzyl Bromide → 7-Benzyloxychromanone

HRID 1600021노트

반응식

HRID 1600021 반응식
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1.[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:13]([O:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

참가 물질

5

반응물 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 2981307-Hydroxychromanone

생성물 1

HCID 144156387-Benzyloxychromanone수율 81.4%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

A mixture of 7-hydroxychromanone (10.0 g, 61 mmol), benzyl bromide (7.6 mL,64 mmol), and potassium carbonate (16.5 g, 120 mmol) in acetone (250 mL) was gently refluxed 24 h. The mixture was cooled and filtered through celite. The filtrate 20 was concentrated and the residue was taken up in ethyl acetate. The organic solution was washed with water and brine, driedover calcium sulfate, and concentrated to a tan solid. Recrystallization from ethanol gave 12.63 g (81%) of 7-benzyloxychromanone as tan crystal which had mp 99°-102° C.; NMR δ7.85 (d, J=9 Hz, 1H), 7.44-7.32 (m,5H), 6.66 (dd, J=2.4, 9Hz, 1H), 6.49 (d, J=2.4 Hz, 1H), 5.09 (s,2H), 4.52 (t, J=6.5 Hz, 2H), 2.76 (t, J=6.5 Hz, 2H).

후처리

  1. temperatureThe mixture was cooled
  2. filtrationfiltered through celite
  3. concentrationThe filtrate 20 was concentrated
  4. washThe organic solution was washed with water and brine, driedover calcium sulfate
  5. concentrationconcentrated to a tan solid
  6. customRecrystallization from ethanol

출처 및 근거

ORD 기록
ord-7cc06498d887470f86c9943aab5eb2ee
출처 데이터셋
uspto-grants-1998_04
특허 번호
US05744483

반응 노트

불러오는 중…