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Trimethylsilylacetylene → HCID 178444321, compound

HRID 399361
Notes
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Reaction equation

HRID 399361 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:13][CH2:12][C@H:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:19][Si:20]([C:23]#[CH:24])([CH3:22])[CH3:21]>C(NC(C)C)(C)C.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>[CH3:19][Si:20]([C:23]#[C:24][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:13][CH2:12][C@H:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1)([CH3:22])[CH3:21]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 178444243HCID 178444243, compound

Product 1

HCID 178444321HCID 178444321, compoundYield 69.3%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476
HCID 178418476, compound
Catalyst
HCID 7912DiisopropylamineSolvent

Procedure

10.00 g (32.36 mmol) of 1-bromo-4-(trans-4-pentylcyclohexyl)benzene, 3.89 g (35.60 mmol) of trimethylsilylacetylene, 0.45 g (0.65 mmol) of bis(triphenylphosphine)palladium(II) chloride and 0.062 g (0.32 mmol) of copper(I) iodide are heated for 6 hours at the reflux temperature in 100 ml of diisopropylamine. The solvent is subsequently stripped off, and the soluble constituents of the residue are chromatographed on silica gel using n-hexane, giving 7.32 g of 1-(trimethylsilylethynyl)-4-(trans-4-pentylcyclohexyl)benzene, ##STR5## which is stirred for 1 hour at room temperature in 220 ml of methanol with 1.38 g (24.70 mmol) of potassium hydroxide. Work-up by evaporation of the solvent, partitioning between ether and water, drying and evaporation of the organic phase gives 4.95 g of 1-ethynyl-4-(trans-4-pentylcyclohexyl)benzene. ##STR6##

Workup

  1. customthe soluble constituents of the residue are chromatographed on silica gel

Sources & evidence

ORD record
ord-41ca4b025a0f4d35a51c7baa48dab03b
Source dataset
uspto-grants-1998_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05820785

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes