Cyclohexanecarboxaldehyde → HCID 178444409, compound

HRID 974157Notes

Reaction equation

HRID 974157 reaction equation
[F:1][C:2]1[CH:9]=[C:8](Br)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH2:11]([CH:16]1[CH2:21][CH2:20][CH:19]([C:22]#[CH:23])[CH2:18][CH2:17]1)[CH2:12][CH2:13][CH2:14][CH3:15].C1(C=O)CCCCC1>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.[Cu]I.C(N(CC)CC)C>[CH2:11]([C@H:16]1[CH2:17][CH2:18][C@H:19]([C:22]#[C:23][C:8]2[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([F:1])[CH:9]=2)[CH2:20][CH2:21]1)[CH2:12][CH2:13][CH2:14][CH3:15]

Participants

7

Reactant 3

HCID 16275CyclohexanecarboxaldehydeHCID 7360294-Bromo-2-fluorobenzonitrileHCID 143657611-Ethynyl-4-pentylcyclohexane

Product 1

HCID 178444409HCID 178444409, compound

Reagents, catalysts & solvents 3

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

Procedure

0.2 mmol of bis-(triphenylphosphine)-palladium(II) chloride and 0.1 mmol of copper(I) iodide are added to a mixture of 0.01 mol of 2-fluoro-4-bromobenzonitrile, 0.01 mol of 4-pentylcyclohexylacetylene (which can be prepared, for example, from the corresponding cyclohexanecarbaldehyde by the method of Corey, Fuchs in Tetrahedron Letters (1972) 3769) and 40 ml of triethylamine at room temperature and the mixture is stirred for 12 hours. The reaction can be monitored with the aid of thin layer chromatography. When the reaction has ended, the suspension is filtered and the filtrate is evaporated. Purification by chromatography and/or crystallization gives 1-(trans-4-pentylcyclohexyl)-2-(3-fluoro-4-cyano- phenyl)-acetylene of M.=38° and C.=40.3°.

Workup

  1. customat room temperature
  2. customThe reaction
  3. filtrationthe suspension is filtered
  4. customthe filtrate is evaporated
  5. customPurification
  6. customby chromatography and/or crystallization

Sources & evidence

ORD record
ord-d4674b18590345c2b02b7ffe229b8031
Source dataset
uspto-grants-1991_11
Patent number
US05068053

Reaction notes

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