Water → 2-Di-n-propylamino-8-(2-trimethylsilylethynyl)-1,2,3,4-tetrahydronaphthalene

HRID 1899597노트

반응식

HRID 1899597 반응식
[CH2:1]([N:4]([CH2:16][CH2:17][CH3:18])[CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[C:8](I)[CH:9]=[CH:10][CH:11]=2)[CH2:6]1)[CH2:2][CH3:3].[CH3:19][Si:20]([C:23]#[CH:24])([CH3:22])[CH3:21].O>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>[CH2:1]([N:4]([CH2:16][CH2:17][CH3:18])[CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[C:8]([C:24]#[C:23][Si:20]([CH3:22])([CH3:21])[CH3:19])[CH:9]=[CH:10][CH:11]=2)[CH2:6]1)[CH2:2][CH3:3]

참가 물질

7

반응물 3

HCID 962WaterHCID 66111TrimethylsilylacetyleneHCID 233735392-Di-n-propylamino-8-iodo-1,2,3,4-tetrahydronaphthalene

생성물 1

HCID 100421182-Di-n-propylamino-8-(2-trimethylsilylethynyl)-1,2,3,4-tetrahydronaphthalene

시약·촉매·용매 3

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

실험 절차

To a solution of 2-di-n-propylamino-8-iodo-1,2,3,4-tetrahydronaphthalene (4.3 g, 12.1 mmol) in triethylamine (100 ml) was added copper(I) iodide (228 mg), bis(triphenylphosphine)palladium(II) chloride (841 mg) and trimethylsilylacetylene (1.7 ml). This mixture was stirred at room temperature overnight. The reaction was poured into water and extracted with ether. The extract was washed with brine, dried (Na2SO4), and concentrated to give 5 g of crude product. Purification by flash chromatography using 20:1 methylene chloride:methanol as solvent gave 4.33 g of 2-di-n-propylamino-8-(2-trimethylsilylethynyl)-1,2,3,4-tetrahydronaphthalene which was used in the next reaction.

후처리

  1. extractionextracted with ether
  2. washThe extract was washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customto give 5 g of crude product
  6. customPurification by flash chromatography

출처 및 근거

ORD 기록
ord-04e8af73649b47b28dcd9e78e26e3946
출처 데이터셋
uspto-grants-1996_11
특허 번호
US05571942

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