Benzyl Bromide → 7-Benzyloxychromanone

HRID 1600021ノート

反応式

HRID 1600021 の反応式
[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

参加物

5

反応物 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 2981307-Hydroxychromanone

生成物 1

HCID 144156387-Benzyloxychromanone収率 81.4%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-7cc06498d887470f86c9943aab5eb2ee
出典データセット
uspto-grants-1998_04
特許番号
US05744483

反応ノート

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