Hydracrylonitrile → 3-(Tert-butyldiphenylsilyloxy)propanenitrile

HRID 385960Notes

Reaction equation

HRID 385960 reaction equation
[OH:1][CH2:2][CH2:3][C:4]#[N:5].CN(C1C=CC=CN=1)C.C(N(CC)CC)C.[C:22]([Si:26](Cl)([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([CH3:25])([CH3:24])[CH3:23]>O1CCCC1>[Si:26]([O:1][CH2:2][CH2:3][C:4]#[N:5])([C:22]([CH3:25])([CH3:24])[CH3:23])([C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 8011HydracrylonitrileHCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 108287163-(Tert-butyldiphenylsilyloxy)propanenitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-hydroxypropanenitrile (1 g, 14.1 mmol), dimethylaminopyridine (0.34 g, 2.8 mmol), and triethylamine (2.9 ml, 21 mmol) in tetrahydrofuran (38 ml) was added tert-butyl(chloro)diphenylsilane (4.3 ml, 16.9 mmol). The mixture was stirred at room temperature overnight. The resulting white slurry was quenched with saturated aqueous ammonium chloride and extracted with ethyl acetate. The combined organics were dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting residue was purified via flash chromatography (silica, 0-17% ethyl acetate in hexane) to afford the title compound. 1H NMR (600 MHz, d6-DMSO): δ 7.65 (dd, 4H), 7.43 (dt, 2H), 7.40 (d, 4H), 3.82 (t, 2H), 2.52 (t, 2H), 1.10 (s, 9H).

Workup

  1. customThe resulting white slurry was quenched with saturated aqueous ammonium chloride
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organics were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified via flash chromatography (silica, 0-17% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-572d4064c4814f9a92ea70f125a0a1b2
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

Loading…