Piperidine → 2-(2-Methyl-4-trimethylsilanylethynylphenoxy)ethanol

HRID 734787Notes

Reaction equation

HRID 734787 reaction equation
I[C:2]1[CH:11]=[CH:10][C:5]([O:6][CH2:7][CH2:8][OH:9])=[C:4]([CH3:12])[CH:3]=1.[CH3:13][Si:14]([C:17]#[CH:18])([CH3:16])[CH3:15].N1CCCCC1.CCOC(C)=O>C1COCC1.O.[Cu]I>[CH3:12][C:4]1[CH:3]=[C:2]([C:18]#[C:17][Si:14]([CH3:16])([CH3:15])[CH3:13])[CH:11]=[CH:10][C:5]=1[O:6][CH2:7][CH2:8][OH:9]

Participants

8

Reactant 4

HCID 8082PiperidineHCID 8857Ethyl AcetateHCID 66111TrimethylsilylacetyleneHCID 40551152-(4-Iodo-2-methyl-phenoxy)-ethanol

Product 1

HCID 690546062-(2-Methyl-4-trimethylsilanylethynylphenoxy)ethanol

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

31 mg (0.160 mmol) of CuI was added under argon to a degassed solution of 2:225 g (8.000 mmol) of 2-(4-iodo-2-methylphenoxy)ethanol, 1.22 mL (8.80 mmol) of trimethylsilylacetylene, 185 mg (0.160 mmol) of tetrakis(triphenylphosphane)palladium, and 2.38 mL (24.00 mmol) of piperidine in 50 mL of THF and the mixture was stirred for 1 hour at RT. The reaction mixture was diluted with water and the aqueous phase was exhaustively extracted with EtOAc. The combined organic phases were washed with saturated aqueous NaCl solution, dried over sodium sulfate, and evaporated down in vacuo. Purification of the crude product by column chromatography (silica gel, cyc/EtOAc 2:1) yielded light brown crystals. Yield: 1.70 g (86% of theoretical); C14H20O2Si (M=248.393); calc.: molpeak (M+H)+: 249; found: molpeak (M+H)+: 249; Rf value: 0.24 (silica gel, cyc/EtOAc 2:1).

Workup

  1. extractionthe aqueous phase was exhaustively extracted with EtOAc
  2. washThe combined organic phases were washed with saturated aqueous NaCl solution
  3. dry with materialdried over sodium sulfate
  4. customevaporated down in vacuo
  5. customPurification of the crude product by column chromatography (silica gel, cyc/EtOAc 2:1)
  6. customyielded light brown crystals

Sources & evidence

ORD record
ord-c764690ff41d47cd9a583fe7f862859c
Source dataset
uspto-grants-2009_09
Patent number
US07592358B2

Reaction notes

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