Diisopropylethylamine → 1-(N,N-bis(trimethylsilyl)amino)-3-trimethylsilylprop-2-yne

HRID 515932Notes

Reaction equation

HRID 515932 reaction equation
N(C(C)C)(C(C)C)CC.[N:10]([CH2:19][C:20]#[CH:21])([Si:15]([CH3:18])([CH3:17])[CH3:16])[Si:11]([CH3:14])([CH3:13])[CH3:12].I[Si:23]([CH3:26])([CH3:25])[CH3:24]>C1(C)C=CC=CC=1>[CH3:16][Si:15]([CH3:18])([CH3:17])[N:10]([CH2:19][C:20]#[C:21][Si:23]([CH3:26])([CH3:25])[CH3:24])[Si:11]([CH3:12])([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 85247Trimethylsilyl iodideHCID 10932630Silanamine, 1,1,1-trimethyl-N-2-propynyl-N-(trimethylsilyl)-2×

Product 1

HCID 131611151-(N,N-bis(trimethylsilyl)amino)-3-trimethylsilylprop-2-yneYield 177.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A reactor with a capacity of 40 mL, equipped with a magnetic stirrer was filled, under argon atmosphere, with 0.0085 g (0.015 mmol) of [{Ir(μ-Cl)(CO)2}2], and then with 25 mL of anhydrous and deoxidized toluene and 0.7 g (5.4 mmol) of NEt(i-Pr)2. The whole mixture was stirred until the starting iridium(I) complex was dissolved, and then 0.598 g (3 mmol) of (Me3Si)2NCH2C≡CH and 0.96 g (4.8 mmol) of ISiMe3 were added to the resulting mixture. The reaction was carried out at a temperature of 80° C. until complete conversion of (Me3Si)2NCH2C≡CH. After the reaction was completed, in order to remove the catalyst from the reaction mixture the solvent was evaporated at a reduced pressure along with any residual unreacted substrates, and then anhydrous pentane was added to the residue. The resulting suspension was filtered and the resulting deposit was rinsed with two portions of a solvent. The solvent was initially evaporated from the filtrate, and the residual product was distilled by means of the “trap-to-trap” technique at a reduced pressure to obtain 1.45 g of 1-(N,N-bis(trimethyl-silyl)amino)-3-trimethylsilylprop-2-yne, obtained with a yield of 96%.

Workup

  1. customA reactor with a capacity of 40 mL, equipped with a magnetic stirrer
  2. dissolutionwas dissolved
  3. customto remove the catalyst from the reaction mixture the solvent
  4. customwas evaporated at a reduced pressure along with any residual unreacted substrates
  5. additionanhydrous pentane was added to the residue
  6. filtrationThe resulting suspension was filtered
  7. washthe resulting deposit was rinsed with two portions of a solvent
  8. customThe solvent was initially evaporated from the filtrate
  9. distillationthe residual product was distilled by means of the “trap-to-trap” technique at a reduced pressure

Sources & evidence

ORD record
ord-05b78b66674f46cc8e7a65e3b093a1ea
Source dataset
uspto-grants-2015_08
Patent number
US09108994B2

Reaction notes

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