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Water → HCID 178447940, compound

HRID 857591
Notes
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Reaction equation

HRID 857591 reaction equation
FC(F)(F)S(O[C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:17]3[CH:22]=[C:21]([F:23])[C:20]([F:24])=[C:19]([F:25])[CH:18]=3)[CH:13]=2)C=1)(=O)=O.[C:28]([CH:30]1[CH2:35][CH2:34][CH:33]([CH2:36][CH2:37][CH3:38])[CH2:32][CH2:31]1)#[CH:29].O.[CH3:40]N(C)C=O>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)I>[CH2:28]([C@H:30]1[CH2:35][CH2:34][C@H:33]([C:36]#[C:37][C:38]2[C:9]3[C:14](=[CH:13][C:12]([C:17]4[CH:18]=[C:19]([F:25])[C:20]([F:24])=[C:21]([F:23])[CH:22]=4)=[CH:11][CH:10]=3)[CH:15]=[CH:16][CH:7]=2)[CH2:32][CH2:31]1)[CH2:29][CH3:40]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 218700436-(3,4,5-Trifluorophenyl)naphthalene-2-yl trifluoromethanesulfonateHCID 218706261-Ethynyl-4-propylcyclohexane

Product 1

HCID 178447940HCID 178447940, compound

Reagents, catalysts & solvents 3

HCID 83717
Copper iodide
Catalyst
HCID 178418397HCID 178418397, compoundCatalyst
HCID 8471TriethylamineSolvent

Conditions

Temperature
50 °C

Procedure

25.0 g of 6-(3,4,5-trifluorophenyl)naphthalene-2-yl trifluoromethanesulfonate and 1-ethynyl-4-propylcyclohexane were dissolved in a mixture of 125 ml of N,N-dimethylformamide and 25 ml of triethylamine. To the solution were then added 0.7 g of tetrakis(triphenylphosphine)palladium and 0.2 g of copper iodide (I). The reaction mixture was then stirred at a temperature of 50° C. for 3 hours. The reaction solution was then allowed to cool to room temperature. To the reaction solution was then added 150 ml of water. The reaction solution was extracted with 200 ml of toluene, washed with water and saturated brine, and then dried over anhydrous sodium sulfate. The solvent was then distilled off. The residue was then recrystallized from ethanol to obtain 17.6 g of 2-(trans-4-propylcyclohexyl)ethynyl-6-(3,4,5-trifluorophenyl)naphthalene.

Workup

  1. temperatureto cool to room temperature
  2. extractionThe reaction solution was extracted with 200 ml of toluene
  3. washwashed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was then distilled off
  6. customThe residue was then recrystallized from ethanol

Sources & evidence

ORD record
ord-8ab84d3100a24c7a85ae7395431a3675
Source dataset
uspto-grants-2006_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07145047B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes