Triphenylphosphine → Methyl 4-trimethylsilylethynylbenzoate

HRID 428212

反応式

HRID 428212 の反応式
Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:31][Si:32]([C:35]#[CH:36])([CH3:34])[CH3:33]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(N(CC)CC)C>[CH3:31][Si:32]([C:35]#[C:36][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1)([CH3:34])[CH3:33]

参加物

6

反応物 3

HCID 11776TriphenylphosphineHCID 12081Methyl 4-bromobenzoateHCID 66111Trimethylsilylacetylene

生成物 1

HCID 640161Methyl 4-trimethylsilylethynylbenzoate

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 8471Triethylamine溶媒

反応条件

温度
90 °C

実験手順

21.5 g (0.1 mol) of methyl 4-bromobenzoate, 300 ml of triethylamine and a mixture of 200 mg of palladium acetate and 400 mg of triphenylphosphine are introduced into a three-necked flask under a stream of nitrogen. 20 g (0.20 mol) of trimethylsilylacetylene are then added, the mixture is heated gradually to 90° C. over 1 hour and left at this temperature for 5 hours. The reaction medium is cooled, the salt is filtered off and the filtrate is evaporated. The residue is taken up in 200 ml of hydrochloric acid (5%) and 400 ml of ethyl ether. The ether phase is separated out after settling has taken place, washed with water, dried over magnesium sulphate and evaporated. The residue obtained is purified by chromatography on a column of silica eluted with dichloromethane. After evaporation of the solvents, 23 g (100%) of the expected derivative are collected in the form of a colourless oil.

後処理

  1. additionare introduced into a three-necked flask under a stream of nitrogen
  2. temperatureThe reaction medium is cooled
  3. filtrationthe salt is filtered off
  4. customthe filtrate is evaporated
  5. customThe ether phase is separated out after settling
  6. washwashed with water
  7. dry with materialdried over magnesium sulphate
  8. customevaporated
  9. customThe residue obtained
  10. customis purified by chromatography on a column of silica
  11. washeluted with dichloromethane
  12. customAfter evaporation of the solvents, 23 g (100%) of the expected derivative
  13. customare collected in the form of a colourless oil

出典と根拠

ORDレコード
ord-8ae874f3257240b28a5afc47c799f4b2
出典データセット
uspto-grants-2001_11
特許番号
US06313162B1

関連ノート

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