Dimethylformamide → Methyl 7-cyano-2,3-dihydro-1-benzoxepine-4-carboxylate

HRID 1277289ノート

反応式

HRID 1277289 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:11][CH2:10][CH2:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][C:6]=2[CH:16]=1.[CH3:17][N:18](C=O)C>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:17]([C:2]1[CH:3]=[CH:4][C:5]2[O:11][CH2:10][CH2:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][C:6]=2[CH:16]=1)#[N:18]

参加物

5

反応物 2

HCID 6228DimethylformamideHCID 22990005Methyl 7-bromo-2,3-dihydro-1-benzooxepine-4-carboxylate

生成物 1

HCID 18472647Methyl 7-cyano-2,3-dihydro-1-benzoxepine-4-carboxylate収率 70%

試薬・触媒・溶媒 2

HCID 11186Zinc cyanide (Zn(CN)2)触媒HCID 178418397HCID 178418397、化合物触媒

反応条件

温度
80 °C

実験手順

A mixture of methyl 7-bromo-2,3-dihydro-1-benzoxepine-4-carboxylate (1416 mg, 5.00 mmol), zinc cyanide (352 mg, 3.00 mmol), tetrakis(triphenylphosphine)palladium (347 mg, 0.30 mmol) and DMF(10 ml) was stirred at 80° C. for 3 hours. The mixture was concentrated under reduced pressure, and to the residue was added ethyl acetate. Insoluble materials were filtered off, which were washed with ethyl acetate. The filtrate was concentrated under reduced pressure. The resulting crude product was recrystallized from ethyl acetate to give methyl 7-cyano-2,3-dihydro-1-benzoxepine-4-carboxylate (800 mg, 3.49 mmol, 70%).

後処理

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionto the residue was added ethyl acetate
  3. filtrationInsoluble materials were filtered off
  4. washwhich were washed with ethyl acetate
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customThe resulting crude product was recrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-f9c2c7a4f1e947d88c9c560efad275bf
出典データセット
uspto-grants-2000_12
特許番号
US06166006

反応ノート

読み込み中…