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

HRID 2228301노트

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HRID 2228301 반응식
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.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 11979704Tetrakis(triphenylphosphine)palladium촉매

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온도
80 °C

실험 절차

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%). IR (KBr): 2222, 1721 cm−1.

후처리

  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

출처 및 근거

ORD 기록
ord-886a025cb6044477a043eb41249a4edc
출처 데이터셋
uspto-grants-2002_07
특허 번호
US06413947B1

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