Water → 4-Chloro-2-cyclohexyl-1-ethynylbenzene

HRID 931854Notes

Reaction equation

HRID 931854 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][Si](C)(C)C)=[C:4]([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[CH:9])=[C:4]([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 70558323HCID 70558323, compound

Product 1

HCID 729429334-Chloro-2-cyclohexyl-1-ethynylbenzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

16.6 g (57.1 mmol) of 8 are dissolved in 154 ml of tetrahydrofuran, cooled to 0° C., and a 1 M solution of tetra-n-butylammonium fluoride (68.48 mmol) is added dropwise. The batch is stirred at room temperature overnight, water is added, the mixture is extracted with methyl t-butyl ether, the organic phase is dried over sodium sulfate and filtered, the solvent is removed in vacuo, and the residue is filtered through silica gel with heptane/toluene, giving the product 9, which is employed in the next step without further purification.

Workup

  1. extractionthe mixture is extracted with methyl t-butyl ether
  2. dry with materialthe organic phase is dried over sodium sulfate
  3. filtrationfiltered
  4. customthe solvent is removed in vacuo
  5. filtrationthe residue is filtered through silica gel with heptane/toluene

Sources & evidence

ORD record
ord-d3fd0a85c9a44e19b7d3894d8666fa4c
Source dataset
uspto-grants-2016_03
Patent number
US09296948B2

Reaction notes

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