Triphenylphosphine → HCID 21263166, 화합물

HRID 567883노트

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HRID 567883 반응식
Br[C:2]1[CH:21]=[CH:20][C:5]2[O:6][C:7]3[CH:15]=[C:14](OC)[CH:13]=[C:12]([O:18]C)[C:8]=3[C:9](=[O:11])[CH2:10][C:4]=2[CH:3]=1.[C:22]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:23]=1.C(N(C(C)C)CC)(C)C>CN1CCCC1=O.C(OCC)(=O)C.[Cu](I)I>[CH2:22]([C:2]1[CH:21]=[CH:20][C:5]2[O:6][C:7]3[CH:15]=[CH:14][CH:13]=[C:12]([OH:18])[C:8]=3[C:9](=[O:11])[CH2:10][C:4]=2[CH:3]=1)[CH3:23]

참가 물질

7

반응물 3

HCID 11776TriphenylphosphineHCID 81531DiisopropylethylamineHCID 23431845HCID 23431845, 화합물

생성물 1

HCID 21263166HCID 21263166, 화합물수율 2,664.1%

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 8857Ethyl Acetate용매HCID 13387N-methyl-2-pyrrolidone용매

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온도
80 °C

실험 절차

2-Bromo-7,9-dimethoxy-10,11-dihydrodibenz[b,f]oxepin-10-one 500 mg (F. W. 349.18, 1.43 mmol) prepared in the first stage of Production Example 79, triphenylphosphine 75 mg (F. W. 262.29, 0.062 mmol), trisbenzyldene acetone dipalladium chloroform complex 74 mg (F. W. 1035.08, 0.015 mmol), diisopropylethylamine 575 μl (F. W. 98.22, d=0.742, 2.86 mmol), ethynyl trimethylsillane 350 μl (F. W. 98.22, d=0.742, 2.86 mmol) and copper iodide 27.5 mg (F. W. 190.44, 0.143 mmol) were dissolved in N-methyl-2-pyrrolidone (5 ml) and, after substituting with argon atmosphere, they were stirred with heating at 80° C. for one hour. The reaction mixture was diluted with ethyl acetate and washed with water and saturated sodium chloride solution. The organic layer was dried and concentrated and the resulting residue was purified by a silica gel column chromatography to give the title compound 420 mg (F. W. 367.419, 66%). The peaks of this compound in 1H-NMR (400 MHz, CDCl3) were as follows.

후처리

  1. washwashed with water and saturated sodium chloride solution
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. customthe resulting residue was purified by a silica gel column chromatography

출처 및 근거

ORD 기록
ord-6d299c3be5b34cc293512871c358c2e4
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06180659B2

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