Trimethylsilylacetylene → 2,2,4,4-Tetramethyl-7-trimethylsilylethynyl-chroman

HRID 2226175노트

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HRID 2226175 반응식
[CH3:1][C:2]1([CH3:15])[CH2:11][C:10]([CH3:13])([CH3:12])[C:9]2[C:4](=[CH:5][C:6](Br)=[CH:7][CH:8]=2)[O:3]1.[CH3:16][Si:17]([C:20]#[CH:21])([CH3:19])[CH3:18]>C(N(CC)CC)C.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][C:2]1([CH3:15])[CH2:11][C:10]([CH3:13])([CH3:12])[C:9]2[C:4](=[CH:5][C:6]([C:21]#[C:20][Si:17]([CH3:19])([CH3:18])[CH3:16])=[CH:7][CH:8]=2)[O:3]1

참가 물질

5

반응물 2

HCID 66111TrimethylsilylacetyleneHCID 18965395HCID 18965395, 화합물2회

생성물 1

HCID 189663522,2,4,4-Tetramethyl-7-trimethylsilylethynyl-chroman

시약·촉매·용매 2

HCID 6102075Dichlorobis(triphenylphosphine)palladium촉매HCID 8471Triethylamine용매

반응 조건

온도
60 °C

실험 절차

A solution of 2 g (7.4 mmol) of 2,2,4,4 tetramethyl-7-bromochroman (Compound 42) and 3.63 g (37.0 mmol) of trimethylsilylacetylene in 5 ml of triethylamine was placed in a heavy walled glass tube and degassed under nitrogen. The mixture was then treated, under nitrogen, with 130 mg (0.6826 mmol) of cuprous iodide and 260 mg (0.3704 mmol) of bis (triphenyl phosphine) palladium (II) chloride. The reaction mixture was degassed again and placed under nitrogen and the tube was sealed. The mixture was heated to 60 degrees C. for 24 hours and then cooled to room temperature and filtered through celite. The solvent was removed in vacuo and the residue purified by flash column chromatography (silica; 2% ethyl acetate/hexane) to give the title compound as a pale yellow solid.

후처리

  1. customdegassed under nitrogen
  2. customThe reaction mixture was degassed again
  3. customthe tube was sealed
  4. temperaturecooled to room temperature
  5. filtrationfiltered through celite
  6. customThe solvent was removed in vacuo
  7. customthe residue purified by flash column chromatography (silica; 2% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-57bc6788d8e04e16900f6bf46a73980f
출처 데이터셋
uspto-grants-1994_09
특허 번호
US05346915

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