Acetonitrile → HCID 58608154, compound

HRID 2243575Notes

Reaction equation

HRID 2243575 reaction equation
I[C:2]1[CH:16]=[CH:15][C:5]([O:6][CH2:7][CH2:8][N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1.C(#N)C.[CH3:20][Si:21]([C:24]#[CH:25])([CH3:23])[CH3:22]>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.C(N(CC)CC)C>[CH3:20][Si:21]([C:24]#[C:25][C:2]1[CH:16]=[CH:15][C:5]([O:6][CH2:7][CH2:8][N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1)([CH3:23])[CH3:22]

Participants

7

Reactant 3

HCID 6342AcetonitrileHCID 66111TrimethylsilylacetyleneHCID 19261706HCID 19261706, compound

Product 1

HCID 58608154HCID 58608154, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
60 °C

Procedure

A resealable tube was charged with 4-[2-(4-iodo-phenoxy)-ethyl]-morpholine 100b (2.00 g, 6.00 mmol), acetonitrile (40 mL), and triethylamine (5 mL). Dichlorobis(triphenylphosphine)palladium (II) (0.211 g, 0.30 mmol), copper (I) iodide (0.057 g, 0.30 mmol), and (trimethylsilyl)acetylene (0.766 g, 1.10 mL, 7.80 mmol) were added. The system was purged with argon, the tube was sealed, and the mixture stirred at 60° C. for 16 h. The reaction mixture was concentrated to afford 4-[2-(4-trimethylsilanylethynyl-phenoxy)-ethyl]-morpholine 101b as a dark brown solid which was used without purification. MS (MH+) 304.2; Calculated 303 for C17H25NO2Si.

Workup

  1. customThe system was purged with argon
  2. customthe tube was sealed
  3. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-fad1ebeb30524bf38e70b631a12a585c
Source dataset
uspto-grants-2010_03
Patent number
US07674907B2

Reaction notes

Loading…