Imidazole → 4-(Tert-butyldimethylsilyloxy)-phenyl-acetonitrile

HRID 899568Notes

Reaction equation

HRID 899568 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][C:7]#[N:8])=[CH:4][CH:3]=1.[Si:11](Cl)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12].N1C=CN=C1>CN(C=O)C.CCOCC>[Si:11]([O:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][C:7]#[N:8])=[CH:4][CH:3]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 265484-Hydroxybenzyl cyanideHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 183335824-(Tert-butyldimethylsilyloxy)-phenyl-acetonitrileYield 98%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 4-hydroxybenzyl cyanide 77 (2.0 g, 15.0 mmol) in DMF (10 ml) was added t-butyldimethylsilyl chloride (2.5 g, 16.5 mmol). The reaction mixture was cooled to 0° C. and imidazole (2.3 g, 33.0 mmol) was added and then the mixture was allowed to warm to ambient temperature. After stirring for 3 hours, the reaction mixture was diluted with ether and washed with 0.5 M HCl, sat. aq. NaHCO3, water, and brine, then dried over MgSO4. The crude product was purified via flash SiO2 (eluted with hexane/ethyl acetate (8:1)) to give 78 as a clear oil (3.6 g, 98% yield). 1H-NMR (400 MHz, chloroform-d) δ 7.87 (d, J=8.5 Hz, 2H), 6.86 (d, J=8.5 Hz, 2H), 3.54 (s, 2H), 0.98 (s, 9H), 0.23 (s, 6H).

Workup

  1. temperatureto warm to ambient temperature
  2. washwashed with 0.5 M HCl, sat. aq. NaHCO3, water, and brine
  3. dry with materialdried over MgSO4
  4. customThe crude product was purified via flash SiO2 (eluted with hexane/ethyl acetate (8:1))

Sources & evidence

ORD record
ord-efe0e2e07f9e4f25b42ecc13e51c3874
Source dataset
uspto-grants-2008_04
Patent number
US07355079B2

Reaction notes

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