Chlorotrimethylsilane → 2-Methyl-2-(trimethylsilyl)propanenitrile

HRID 1648966Notes

Reaction equation

HRID 1648966 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.CCCCCC.[C:19](#[N:23])[CH:20]([CH3:22])[CH3:21].Cl[Si:25]([CH3:28])([CH3:27])[CH3:26]>C1COCC1>[CH3:26][Si:25]([CH3:28])([CH3:27])[C:20]([CH3:22])([CH3:21])[C:19]#[N:23]

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 6559IsobutyronitrileHCID 7912DiisopropylamineHCID 178418244HCID 178418244, compound

Product 1

HCID 130879332-Methyl-2-(trimethylsilyl)propanenitrileYield 74.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(Trimethylsilyl)isobutyronitrile was prepared by the following procedure. To a stirred solution of 30.2 g (0.29 mole) of diisopropylamine in 220 ml of THF under argon was added at 0°-5° 184 ml of 1.58 M n-butyl lithium/hexane at a rate such that the temperature did not exceed 6°. After 15 min. 20 g (0.29 mole) of isobutyronitrile was added at 0°-5°. After 20 min., 47.3 g (0.44 mole) of chlorotrimethylsilane was added. After standing 18 h at room temperature, the mixture was filtered under argon and the filtrate was evaporated in vacuo to a solid which was extracted with ether and filtered. The filtrate was evaporated in vacuo to give 30.51 g (74%) of 2-(trimethysilyl)isobutyronitrile as a pale yellow watersensitive solid. Anal. Calcd. for C7H15NS: C, 59.50; H, 10.70; N, 9.92. Found: C, 59.60; H, 11.07; N, 9.74. I.R. (CCl4): 2220 cm-1 (C≡N), 847 cm-1, 1255 cm-1 (SiMe3). NMR (90 MHz): δ0.22 (9H, SiCH3); δ1.35 (6H, CCH3).

Workup

  1. custom2-(Trimethylsilyl)isobutyronitrile was prepared by the following procedure
  2. customdid not exceed 6°
  3. waitAfter 20 min.
  4. waitAfter standing 18 h at room temperature
  5. filtrationthe mixture was filtered under argon
  6. customthe filtrate was evaporated in vacuo to a solid which
  7. extractionwas extracted with ether
  8. filtrationfiltered
  9. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-4b05340ae7fb4f2ea8abb4898727afae
Source dataset
uspto-grants-1983_11
Patent number
US04414372

Reaction notes

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