Hydrochloric Acid → HCID 59408349, compound

HRID 2389206Notes

Reaction equation

HRID 2389206 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][CH:11]([CH:14]3[CH2:19][CH2:18][CH:17]([CH2:20][CH2:21][CH3:22])[CH2:16][CH2:15]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH:23]#[C:24][CH2:25][CH2:26][CH3:27].Cl>CCN(CC)CC.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:23]([C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][CH:11]([CH:14]3[CH2:19][CH2:18][CH:17]([CH2:20][CH2:21][CH3:22])[CH2:16][CH2:15]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1)#[C:24][CH2:25][CH2:26][CH3:27]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 123091-PentyneHCID 15135318HCID 15135318, compound

Product 1

HCID 59408349HCID 59408349, compound

Reagents, catalysts & solvents 3

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

Procedure

8.0 g (22.0 mmol) of 4′-(4-bromophenyl)-4-propylbicyclohexyl are stirred at 60° C. for 60 h in 80 ml of NEt3 together with 4.4 ml (44.0 mmol) of 1-pentyne in the presence of 309 mg (0.44 mmol) of bis(triphenylphosphine)palladium(II) chloride and 42 mg (0.22 mmol) of copper(I) iodide. The batch is added to ice-water and acidified using hydrochloric acid. The mixture is extracted with MTBE, and the combined organic phases are washed with water and sat. sodium chloride solution. The solution is concentrated to completion, and the crude product is purified by column chromatography (SiO2, n-heptane). The further purification is carried out by recrystallisation from n-heptane (−20° C.). This gives 4′-(4-pent-1-ynylphenyl)-4-propylbicyclohexyl as a colourless solid (m.p. 47° C.).

Workup

  1. extractionThe mixture is extracted with MTBE
  2. washthe combined organic phases are washed with water and sat. sodium chloride solution
  3. concentrationThe solution is concentrated to completion
  4. customthe crude product is purified by column chromatography (SiO2, n-heptane)
  5. customThe further purification
  6. customis carried out by recrystallisation from n-heptane (−20° C.)

Sources & evidence

ORD record
ord-1661b0f2a77446fd9d54e8978a1baed2
Source dataset
uspto-grants-2012_09
Patent number
US08273264B2

Reaction notes

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