Hydracrylonitrile → 3-(Tert-butyldiphenylsilyloxy)propanenitrile

HRID 1432013Notes

Reaction equation

HRID 1432013 reaction equation
[OH:1][CH2:2][CH2:3][C:4]#[N:5].CCN(CC)CC.[CH3:13][C:14]([Si:17](Cl)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([CH3:16])[CH3:15]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Si:17]([O:1][CH2:2][CH2:3][C:4]#[N:5])([C:14]([CH3:16])([CH3:15])[CH3:13])([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 8011HydracrylonitrileHCID 8471TriethylamineHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 108287163-(Tert-butyldiphenylsilyloxy)propanenitrile

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-hydroxypropanenitrile (7.1 g, 0.1 mol) and DMAP (1.22 g, 0.01 mmol) in dry DCM (30 mL) at room temperature was added NEt3 (30.3 g, 0.3 mol), followed by TBDPSCl (27.5 g, 0.1 mol). A lot of white solid appeared. After stirring at room temperature overnight, the reaction mixture was quenched with sat. NH4Cl solution, extracted with DCM, dried over Na2SO4, and evaporated in vacuo. Flash chomatography (SiO2, hexane/EtOAc=100:2 to 100:5 to 100:10) of the crude material gave the title compound as a white solid.

Workup

  1. customthe reaction mixture was quenched with sat. NH4Cl solution
  2. extractionextracted with DCM
  3. dry with materialdried over Na2SO4
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-6950f317ece74b549c50cb2329207854
Source dataset
uspto-grants-2009_11
Patent number
US07612060B2

Reaction notes

Loading…