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

HRID 1647831노트

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HRID 1647831 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].C(N(CC)CC)C.[CH3:26][Si:27]([C:30]#[CH:31])([CH3:29])[CH3:28]>[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.O>[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:31]#[C:30][Si:27]([CH3:29])([CH3:28])[CH3:26])[CH:9]=[CH:10][CH:11]=2)[CH2:6]1)[CH2:2][CH3:3]

참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 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 962Water용매

실험 절차

To a solution of 2-(Di-n-propylamino)-8-iodo-1,2,3,4-tetrahydronaphthalene (4.3 g, 12.1 mmol), as prepared in co-pending U.S. application Ser. No. 07/653,583 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-418504136bc24eb0876c6fad498ee21b
출처 데이터셋
uspto-grants-1995_07
특허 번호
US05434174

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