Trimethylsilylacetylene → Trimethylsilyl (4,4,7-trimethyl-thiochroman-6-yl) ethyne

HRID 6536

반응식

HRID 6536 반응식
[CH3:1][C:2]1([CH3:14])[C:11]2[C:6](=[CH:7][C:8]([CH3:13])=[C:9](Br)[CH:10]=2)[S:5][CH2:4][CH2:3]1.[CH3:15][Si:16]([C:19]#[CH:20])([CH3:18])[CH3:17]>[Pd+2].[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.C(N(CC)CC)C>[CH3:1][C:2]1([CH3:14])[C:11]2[C:6](=[CH:7][C:8]([CH3:13])=[C:9]([C:20]#[C:19][Si:16]([CH3:18])([CH3:17])[CH3:15])[CH:10]=2)[S:5][CH2:4][CH2:3]1

참가 물질

6

반응물 2

HCID 66111TrimethylsilylacetyleneHCID 156611176-Bromo-4,4,7-trimethylthiochroman2회

생성물 1

HCID 15661126Trimethylsilyl (4,4,7-trimethyl-thiochroman-6-yl) ethyne

시약·촉매·용매 3

HCID 105144Allyl(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)chloropalladium(II)촉매HCID 6102075Dichlorobis(triphenylphosphine)palladium촉매HCID 8471Triethylamine용매

반응 조건

온도
85 °C

실험 절차

A mixture of 624 mg (3.0 mmol) of 4,4,7-trimethyl-6-bromothiochroman (Compound 66) 314 mg (3.2 mmol) of trimethylsilyl acetylene, 40 mg (0.21 mmol) of cuprous iodide, 80 mg (0.11 mmol) of bis (triphenylphosphin) palladium (II) chloride and 1 ml of triethylamine was degassed under nitrogen and heated in a sealed tube at 85 degrees C. for 15 h. The mixture was then treated with a further 20 mg (0.11 mmol) of cuprous iodide and 40 mg (0.06 mmol) of the palladium (II) catalyst. The mixture was then heated under a nitrogen atmosphere in the sealed tube at 100 degrees C. for a further 64 h. The triethylamine was then removed under vacuum and the residue purified by flash chromatography (silica; hexanes) to give the title compound as a yellow oil. PMR (CDCl3) δ 0.28 (9H, s), 1.30 (6H, s), 1.88-1.97 (2H, m), 2.33 (3H, s), 2.97-3.05 (2H, m), 6.92 (1H, s), 7.43 (1H, s).

후처리

  1. customwas degassed under nitrogen
  2. temperatureThe mixture was then heated under a nitrogen atmosphere in the sealed tube at 100 degrees C
  3. waitfor a further 64 h
  4. customThe triethylamine was then removed under vacuum
  5. customthe residue purified by flash chromatography (silica; hexanes)

출처 및 근거

ORD 기록
ord-3d9d382e9f8f4afa9b0c7a2622b789ae
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05248777

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