Triphenylphosphine → 1-(3-Bromo-4-{[(4-chloro-2-pyridinyl)methyl]oxy}phenyl)ethanone

HRID 63272

反応式

HRID 63272 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][OH:9])[CH:3]=1.[Br:10][C:11]1[CH:12]=[C:13]([C:18](=[O:20])[CH3:19])[CH:14]=[CH:15][C:16]=1O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[Br:10][C:11]1[CH:12]=[C:13]([C:18](=[O:20])[CH3:19])[CH:14]=[CH:15][C:16]=1[O:9][CH2:8][C:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[CH:6][N:5]=1

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 6080941-(3-Bromo-4-hydroxyphenyl)ethanoneHCID 2763167(4-Chloropyridin-2-yl)methanolHCID 5462977Diethyl azodicarboxylate

生成物 1

HCID 682019601-(3-Bromo-4-{[(4-chloro-2-pyridinyl)methyl]oxy}phenyl)ethanone

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of (4-chloro-2-pyridinyl)methanol (Commercial eg Aldrich) (0.2 g) in THF (5 ml) were added 1-(3-bromo-4-hydroxyphenyl)ethanone (0.3 g) and triphenylphosphine (0.547 g). This was stirred for 10 min before cooling and adding slowly DEAD (0.363 g). This was stirred for 16 h. The reaction mixture was partitioned between water and ethyl acetate. The aqueous was reextracted with ethyl acetate and the combined organics were washed with brine, dried over sodium sulfate and concentrated in vacuo. This was purified through silica eluting with 0-35% ethyl acetate in hexane to give the title compound, 0.30 g

後処理

  1. temperaturebefore cooling
  2. stirringThis was stirred for 16 h
  3. customThe reaction mixture was partitioned between water and ethyl acetate
  4. washthe combined organics were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThis was purified through silica eluting with 0-35% ethyl acetate in hexane

出典と根拠

ORDレコード
ord-a429b1da3344417d94b8f0ecf4efed2d
出典データセット
uspto-grants-2016_09
特許番号
US09447074B2

関連ノート

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