Water → HCID 70558323, compound

HRID 931853Notes

Reaction equation

HRID 931853 reaction equation
FC(F)(F)S(O)(=O)=O.[Cl:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[CH:11]=1.[CH3:22][Si:23]([C:26]#[CH:27])([CH3:25])[CH3:24].C(N(CC)CC)C.O>CN(C)C=O.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>[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([C:27]#[C:26][Si:23]([CH3:25])([CH3:24])[CH3:22])=[C:12]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[CH:11]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 866691204-Chloro-2-cyclohexylbenzene trifluoromethanesulfonate

Product 1

HCID 70558323HCID 70558323, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

21 g (61.3 mmol) of 7, 25.8 ml (183.8 mmol) of trimethylsilylacetylene, 2.15 g (3 mmol) of bis(triphenylphosphine)palladium(II) chloride and 21.2 ml (153.2 mmol) of triethylamine are dissolved in 60 ml of N,N-dimethylformamide under nitrogen, and the mixture is heated at 100° C. overnight. 100 ml of water are added to the cooled solution, and the mixture is extracted twice with methyl t-butyl ether (100 ml). The combined organic phases are washed with water, dried over sodium sulfate and evaporated in vacuo. The residue is purified by column chromatography, giving the product 8, which is employed in the next step without further purification.

Workup

  1. extractionthe mixture is extracted twice with methyl t-butyl ether (100 ml)
  2. washThe combined organic phases are washed with water
  3. dry with materialdried over sodium sulfate
  4. customevaporated in vacuo
  5. customThe residue is purified by column chromatography

Sources & evidence

ORD record
ord-33171a7aa82e44a5a6ec294b024c4b19
Source dataset
uspto-grants-2016_03
Patent number
US09296948B2

Reaction notes

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