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Trimethylsilylacetylene → 4,4-Dimethyl-2-oxo-1,2,3,4-tetrahydro-1-isopropyl-7-[(trimethylsilyl)ethynyl]quinoline

HRID 52450
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HRID 52450 반응식
[CH3:1][C:2]1([CH3:17])[C:11]2[C:6](=[CH:7][C:8](Br)=[CH:9][CH:10]=2)[N:5]([CH:13]([CH3:15])[CH3:14])[C:4](=[O:16])[CH2:3]1.[CH3:18][Si:19]([C:22]#[CH:23])([CH3:21])[CH3:20]>C(N(CC)CC)C.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:1][C:2]1([CH3:17])[C:11]2[C:6](=[CH:7][C:8]([C:23]#[C:22][Si:19]([CH3:21])([CH3:20])[CH3:18])=[CH:9][CH:10]=2)[N:5]([CH:13]([CH3:15])[CH3:14])[C:4](=[O:16])[CH2:3]1
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참가 물질

6

반응물 2

HCID 66111TrimethylsilylacetyleneHCID 232919127-Bromo-1-isopropyl-4,4-dimethyl-2-oxo-1,2,3,4-tetrahydroquinoline2회

생성물 1

HCID 199637194,4-Dimethyl-2-oxo-1,2,3,4-tetrahydro-1-isopropyl-7-[(trimethylsilyl)ethynyl]quinoline

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매
HCID 178418476
HCID 178418476, 화합물
촉매
HCID 8471Triethylamine용매

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온도
50 °C

실험 절차

To a solution of 0.40 g (1.36 mmol) of 4,4-dimethyl-2-oxo-1,2,3,4-tetrahydro-1-iso-propyl-7-bromoquinoline (Compound 24) in 5.0 ml of triethylamine which was degassed under argon for 15 min in a sealable tube, were added successively 0.069 g (0.36 mmol) of copper(I)iodide, (1.0 ml, 7.1 mmol) of (trimethylsilyl)acetylene, and 0.147 g (0.21 mmol) of bis(triphenylphosphine)palladium(II) chloride. The reaction mixture was degassed for an additional 5 min. The tube was sealed and the reaction mixture was heated at 50° C. for 72 h. The reaction mixture was concentrated in vacuo. Purification by flash chromatography (silica, 10% ethyl acetate in hexane) gave the title compound as an oil. PNMR (CDCl3) d 0.25 (9H, s), 1.26 (6H, s), 1.54 (6H, d, J=7.1 Hz), 2.39 (2H, s), 4.60 (1H, p, J=7.1 Hz), 7.17 (3H, m).

후처리

  1. customThe reaction mixture was degassed for an additional 5 min
  2. customThe tube was sealed
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customPurification by flash chromatography (silica, 10% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-7007ca7dcc814998aaf55b4715f21371
출처 데이터셋
uspto-grants-1997_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05616712

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