Boron trifluoride etherate → Dibenz[b,e]oxepin-11(6H)-one

HRID 718118

反応式

HRID 718118 の反応式
[O:1]([CH2:8][C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.B(F)(F)F.CCOCC>C(Cl)Cl>[CH:4]1[C:3]2[C:11](=[O:13])[C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[CH2:8][O:1][C:2]=2[CH:7]=[CH:6][CH:5]=1

参加物

5

反応物 3

HCID 8000Boron trifluoride etherateHCID 9845Trifluoroacetic anhydrideHCID 697612-(Phenoxymethyl)benzoic acid

生成物 1

HCID 78259Dibenz[b,e]oxepin-11(6H)-one収率 98%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
40 °C

実験手順

The 2-(phenoxymethyl)benzoic acid (22.18 g, 97 mmol) was dissolved in DCM (200 mL) and trifluoroacetic anhydride (20.59 mL, 146 mmol) was added, followed by a catalytic amount of borontrifluoride etherate (2.22 mL, 17.5 mmol). The reaction mixture was heated at 40° C. for 2 hours. The solution was then washed with water, sodium bicarbonate (saturated solution) and water. The organic phases was dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified on silica gel (10-20% ethyl acetate in hexanes) to afford title compound 482 (19.937 g, 98%) as a light pink solid. MS (m/z): 211.1 (M+H).

後処理

  1. washThe solution was then washed with water, sodium bicarbonate (saturated solution) and water
  2. dry with materialThe organic phases was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified on silica gel (10-20% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-66b607ca772f4e40bce4652b7021ae2c
出典データセット
uspto-grants-2015_11
特許番号
US09193749B2

関連ノート

読み込み中…