tert-Butyldimethylsilyl chloride → 3-(Tert-butyldimethylsilyloxy)-3-(3-nitrophenyl)propanenitrile

HRID 716773Notes

Reaction equation

HRID 716773 reaction equation
[CH3:1][C:2]([Si:5](Cl)([CH3:7])[CH3:6])([CH3:4])[CH3:3].[OH:9][CH:10]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=1)[CH2:11][C:12]#[N:13]>CN(C=O)C>[Si:5]([O:9][CH:10]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=1)[CH2:11][C:12]#[N:13])([C:2]([CH3:4])([CH3:3])[CH3:1])([CH3:7])[CH3:6]

Participants

4

Reactant 2

HCID 28928tert-Butyldimethylsilyl chlorideHCID 593169073-Hydroxy-3-(3-nitrophenyl)propanenitrile

Product 1

HCID 672965323-(Tert-butyldimethylsilyloxy)-3-(3-nitrophenyl)propanenitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

TBDMS-Cl (2.7 g, 18.24 mmol) was added at 0° C. to a stirred solution of aniline 11 (3 g, 15.62 mmol) and TEA (1.73 g, 17.18 mmoles) in DMF and the reaction mixture was stirred at RT for 4 h. The reaction mixture was partitioned between EtOAc and water. Organic layer was washed with water 2×, dried over sodium sulfate and concentrated under reduced pressure to give 3(tert-butyldimethylsilyloxy)-3-(3-nitrophenyl)propanenitrile as colorless liquid. Yield (4.0 g, 83%); 1H NMR (400 MHz, DMSO-d6) δ 8.31 (s, 1H), 8.18 (d, J=7.6 Hz, 1H), 7.88 (d, J=7.6 Hz, 1H), 7.70 (t, J=7.6 Hz, 1H), 5.33 (t, J=5.6 Hz, 1H), 3.01-2.92 (m, 2H), 0.88 (s, 9H), 0.13 (s, 3H), −0.05 (s, 3H).

Workup

  1. customThe reaction mixture was partitioned between EtOAc and water
  2. washOrganic layer was washed with water 2×
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a8867b768eb841db89c93b77c52232c2
Source dataset
uspto-grants-2015_11
Patent number
US09193669B2

Reaction notes

Loading…