Water → HCID 178445629, compound

HRID 1608894Notes

Reaction equation

HRID 1608894 reaction equation
[CH2:1]([C:4]1[CH:9]=[C:8]([F:10])[C:7](I)=[C:6]([F:12])[CH:5]=1)[CH2:2][CH3:3].[CH2:13]([C@H:17]1[CH2:22][CH2:21][C@H:20]([C@H:23]2[CH2:28][CH2:27][C@H:26]([C:29]#[CH:30])[CH2:25][CH2:24]2)[CH2:19][CH2:18]1)[CH2:14][CH:15]=[CH2:16].C(N(CC)CC)C.O>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.CCOCC>[CH2:13]([C@H:17]1[CH2:22][CH2:21][C@H:20]([C@H:23]2[CH2:24][CH2:25][C@H:26]([C:29]#[C:30][C:7]3[C:8]([F:10])=[CH:9][C:4]([CH2:1][CH2:2][CH3:3])=[CH:5][C:6]=3[F:12])[CH2:27][CH2:28]2)[CH2:19][CH2:18]1)[CH2:14][CH:15]=[CH2:16]

Participants

8

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 18979647HCID 18979647, compoundHCID 178455758HCID 178455758, compound

Product 1

HCID 178445629HCID 178445629, compoundYield 70.1%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 0.65 g of 1-propyl-3,5-difluoro-4-iodobenzene (prepared according to Example 1a), 0.56 g of trans-4-[trans-4-(3-butenyl)cyclohexyl]cyclohexylacetylene, 0.053 g of tetrakis(triphenylphosphine)palladium (0), 0.009 g of copper(I) iodide and 6 ml of triethylamine was heated to 90° C. for 17 hrs. The reaction mixture was cooled, partioned between water and ether, the organic phase was separated and the aqueous phase was extracted several times with ether. The combined organic phases were dried over magnesium sulphate, filtered and evaporated. chromatography of the residue on silica gel with hexane and two-fold crystallization, firstly from hexane and then from isopropanol, gave 640 mg of 1-{trans-4-[trans-4-(3-butenyl)cyclohexyl]cyclohexylethynyl}-2,6-difluoro-4-propylbenzene, m.p. (C/N) 48.5° C., cl.p. (N/I) 189.8° C.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customthe organic phase was separated
  3. extractionthe aqueous phase was extracted several times with ether
  4. dry with materialThe combined organic phases were dried over magnesium sulphate
  5. filtrationfiltered
  6. customevaporated
  7. customchromatography of the residue on silica gel with hexane and two-fold crystallization

Sources & evidence

ORD record
ord-ab07ef6c16fb4eca8dc0bbd7161b8344
Source dataset
uspto-grants-1995_03
Patent number
US05399292

Reaction notes

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