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

HRID 2226117ノート

反応式

HRID 2226117 の反応式
[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

参加物

5

反応物 2

HCID 66111TrimethylsilylacetyleneHCID 18965395HCID 18965395、化合物2 回

生成物 1

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

試薬・触媒・溶媒 2

HCID 6102075Dichlorobis(triphenylphosphine)palladium触媒HCID 8471Triethylamine溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-952368d81c944e21929a71ff0ea79403
出典データセット
uspto-grants-1994_09
特許番号
US05346895

反応ノート

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