Triphenylphosphine → HCID 69991334、化合物

HRID 2299188ノート

反応式

HRID 2299188 の反応式
Br[C:2]1[CH:21]=[CH:20][C:5]2[O:6][C:7]3[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[C:12]([O:18][CH3:19])[C:8]=3[C:9](=[O:11])[CH2:10][C:4]=2[CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(C(C)C)CC)(C)C.[C:50]([Si:52]([CH3:55])([CH3:54])[CH3:53])#[CH:51]>CN1CCCC1=O.C(OCC)(=O)C.[Cu](I)I>[CH3:17][O:16][C:14]1[CH:13]=[C:12]([O:18][CH3:19])[C:8]2[C:9](=[O:11])[CH2:10][C:4]3[C:3]([C:51]#[C:50][Si:52]([CH3:55])([CH3:54])[CH3:53])=[CH:2][CH:21]=[CH:20][C:5]=3[O:6][C:7]=2[CH:15]=1

参加物

8

反応物 4

HCID 11776TriphenylphosphineHCID 66111TrimethylsilylacetyleneHCID 81531DiisopropylethylamineHCID 23431845HCID 23431845、化合物

生成物 1

HCID 69991334HCID 69991334、化合物収率 80.1%

試薬・触媒・溶媒 3

HCID 83717Copper iodide触媒HCID 8857Ethyl Acetate溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
80 °C

実験手順

2-Bromo-7,9-dimethoxy-10,11-dihydrodibenzo[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), trisbenzylidene 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 trimethylsilane 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.

後処理

  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

出典と根拠

ORDレコード
ord-6b168829bccc495ea8f058e912065a65
出典データセット
uspto-grants-2002_12
特許番号
US06495592B1

反応ノート

読み込み中…