Imidazole → 3-(Tert-butyldiphenylsilyloxy)propanenitrile

HRID 964564Notes

Reaction equation

HRID 964564 reaction equation
[OH:1][CH2:2][CH2:3][C:4]#[N:5].N1C=CN=C1.[Si:11](Cl)([C:24]([CH3:27])([CH3:26])[CH3:25])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1COCC1>[Si:11]([O:1][CH2:2][CH2:3][C:4]#[N:5])([C:24]([CH3:27])([CH3:26])[CH3:25])([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 8011HydracrylonitrileHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 108287163-(Tert-butyldiphenylsilyloxy)propanenitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Hydroxyproprionitrile (7.11 g, 100 mmol) and imidazole (68.08 g, 100 mmol) in dry THF (100 ml) was stirred at room temperature for 45 mins and tert-butyldiphenylsilylchloride (28.86 g, 105 mmol) was added slowly by syringe over 10 mins. The clear solution was stirred at room temperature overnight during which time a white precipitate formed. The reaction was filtered and the filtrate evaporated in vacuo to leave an oil which was chromatographed on silica (eluting with 10% petrol in ether) to give the product as a clear slightly yellow oil (31.41 g, quant.) δH (CDCl3) 7.76-7.65 (4H, m, PhH4), 7.48-7.35 (6H, m, PhH6), 3.86 (2H, t, J 6.5, OCH2CH2CN), 2.54 (2H, t, J 6.5, OCH2 CH2CN), 1.09 (9H, s, tert-Bu).

Workup

  1. customformed
  2. filtrationThe reaction was filtered
  3. customthe filtrate evaporated in vacuo
  4. customto leave an oil which
  5. customwas chromatographed on silica (eluting with 10% petrol in ether)
  6. customto give the product as a clear slightly yellow oil (31.41 g, quant.) δH (CDCl3) 7.76-7.65 (4H, m, PhH4), 7.48-7.35 (6H, m, PhH6), 3.86 (2H, t, J 6.5, OCH2CH2CN), 2.54 (2H, t, J 6.5, OCH2 CH2CN), 1.09 (9H, s, tert-Bu)

Sources & evidence

ORD record
ord-483b09509e6347b9bced7d9830de4b36
Source dataset
uspto-grants-1998_06
Patent number
US05770598

Reaction notes

Loading…