HCID 178447924, compound → HCID 178447958, compound

HRID 1608893Notes

Reaction equation

HRID 1608893 reaction equation
[CH2:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([C:10]2[CH:15]=[C:14]([F:16])[C:13](I)=[C:12]([F:18])[CH:11]=2)[CH2:6][CH2:5]1)[CH2:2][CH3:3].[C:19]([C@H:21]1[CH2:26][CH2:25][C@H:24]([CH2:27][CH2:28][CH3:29])[CH2:23][CH2:22]1)#[CH:20]>C(N(CC)CC)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[CH2:27]([C@H:24]1[CH2:23][CH2:22][C@H:21]([C:19]#[C:20][C:13]2[C:14]([F:16])=[CH:15][C:10]([C@H:7]3[CH2:8][CH2:9][C@H:4]([CH2:1][CH2:2][CH3:3])[CH2:5][CH2:6]3)=[CH:11][C:12]=2[F:18])[CH2:26][CH2:25]1)[CH2:28][CH3:29]

Participants

6

Reactant 2

HCID 178447924HCID 178447924, compoundHCID 178455741HCID 178455741, compound

Product 1

HCID 178447958HCID 178447958, compoundYield 44.3%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of 0.8 g of 1-(trans-4-propylcyclohexyl)-3,5-difluoro-4-iodobenzene, 0.379 g of trans-1-ethynyl-4-propylcyclohexane, 0.023 g of tetrakis(triphenylphosphine)palladium(0) and 0.009 g of copper(I) iodide in 20 ml of triethylamine is stirred at 105° C. for 17 hrs. Thereafter, the mixture is cooled, partitioned between ether and water, the combined organic phases are dried over magnesium sulphate, filtered and the filtrate is evaporated on a rotary evaporator. Chromatography on 140 g of silica gel with hexane and three-fold crystallization from methanol, hexane and again methanol gives 0.376 g of 1-(trans-4-propylcyclohexylethynyl)-2,6-difluoro-4-(trans-4-propylcyclohexyl)benzene, m.p. (C/N) 120.2° C., cl.p. (N/I) 171.4° C.

Workup

  1. temperatureThereafter, the mixture is cooled
  2. custompartitioned between ether and water
  3. dry with materialthe combined organic phases are dried over magnesium sulphate
  4. filtrationfiltered
  5. customthe filtrate is evaporated on a rotary evaporator
  6. customChromatography on 140 g of silica gel with hexane and three-fold crystallization from methanol, hexane and again methanol

Sources & evidence

ORD record
ord-fb8c3d2bee05449386d837fd3a875f98
Source dataset
uspto-grants-1995_03
Patent number
US05399292

Reaction notes

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