Diethylamine → HCID 15199168, compound

HRID 2260876Notes

Reaction equation

HRID 2260876 reaction equation
N([CH2:4][CH3:5])CC.[CH3:6][Si:7]([C:10]#[CH:11])([CH3:9])[CH3:8].[CH2:12]([S:19]/[C:20](/I)=[CH:21]\[CH:22]=[C:23](/[S:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)\I)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Al]>[Cu]I.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OCC)(=O)C.C(Cl)Cl.C1C=CC=CC=1>[CH3:6][Si:7]([CH3:9])([CH3:8])[C:10]#[C:11]/[C:23](/[S:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[CH:22]/[CH:21]=[C:20](\[S:19][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)/[C:5]#[C:4][Si:7]([CH3:9])([CH3:8])[CH3:6]

Participants

10

Reactant 4

HCID 8021DiethylamineHCID 66111TrimethylsilylacetyleneHCID 5359268AluminumHCID 15199166HCID 15199166, compound

Product 1

HCID 15199168HCID 15199168, compoundYield 71%

Reagents, catalysts & solvents 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 241BenzeneSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of CuI (4.7 mg. 0.02 mmol), bis(triphenylphosphine) palladium (II) chloride (7.7 mg, 0.01 mmol), Et2NH (2 mL), trimethylsilylethyne (80 mL, 0.546 mmol), 6 (100 mg, 0.182 mmol), and dry benzene (1.5 mL) was stirred for 48 h at room temperature under argon in a flask wrapped with aluminum foil. Analysis by TLC (1:4 CH2Cl2 :hexanes) indicated the disappearance of starting compound. The solution was concentrated in vacuo, and water (10 mL) and ether (25 mL) were added to the residue. The layers were separated, the aqueous layer was extracted with ether (2×10 mL), the combined ether layers were washed with water (2×10 mL), dried (MgSO4), and concentrated in vacuo. Flash column chromatography of the residue (2.5:97.5 ethyl acetate: hexanes) afforded 12 as a pale yellow solid (63.3 mg, yield 71%): 1H NMR δ 7.2-7.5 (m, 12 H), 6.97 (s, 2 H), 4.15 (s, 4 H), 0.25 (s, 18 H); 13C NMR δ 137.76, 131.83, 128.92, 128.58, 128.27, 121.15, 102.43, 101.78, 37.37, -0.09; Anal. Calcd for C28H34S2Si2, C, 68.51; H, 6.98. Found, C, 68.57; H, 7.02.

Workup

  1. concentrationThe solution was concentrated in vacuo, and water (10 mL) and ether (25 mL)
  2. additionwere added to the residue
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with ether (2×10 mL)
  5. washthe combined ether layers were washed with water (2×10 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-731a69b07106405798f2ee41ba700edf
Source dataset
uspto-grants-1995_12
Patent number
US05478959

Reaction notes

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