Triphenylphosphine → Methyl 4-trimethylsilylethynylbenzoate

HRID 428212

반응식

HRID 428212 반응식
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]

참가 물질

6

반응물 3

HCID 11776TriphenylphosphineHCID 12081Methyl 4-bromobenzoateHCID 66111Trimethylsilylacetylene

생성물 1

HCID 640161Methyl 4-trimethylsilylethynylbenzoate

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 8471Triethylamine용매

반응 조건

온도
90 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8ae874f3257240b28a5afc47c799f4b2
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06313162B1

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