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

HRID 22143Notes

Reaction equation

HRID 22143 reaction equation
[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]

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-01693ebdc6c24949ada3b48f1af18635
Source dataset
uspto-grants-1995_06
Patent number
US05426226

Reaction notes

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