Tetrahydrofuran → 2-(4-Formyl-3-methylphenyl)-2-methylpropanenitrile

HRID 603141Notes

Reaction equation

HRID 603141 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:12])([CH3:11])[C:9]#[N:10])=[CH:4][C:3]=1[CH3:13].[Li]C(C)(C)C.C1C[O:22][CH2:21]C1>>[CH:21]([C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:12])([CH3:11])[C:9]#[N:10])=[CH:4][C:3]=1[CH3:13])=[O:22]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 582984722-(4-Bromo-3-methylphenyl)-2-methylpropanenitrileHCID 178418306HCID 178418306, compound

Product 1

HCID 582984532-(4-Formyl-3-methylphenyl)-2-methylpropanenitrileYield 73%

Conditions

Temperature
-78 °C

Procedure

2-(4-bromo-3-methylphenyl)-2-methylpropanenitrile (3.31 g, 13.9 mmol) is dissolved in dry THF (80 mL). The mixture is cooled to −78° C. and tert-BuLi (1.7 M in pentane, 18 mL, 30.6 mmol) is added. After 30 minutes, the reaction is quenched with DMF (10 mL), volatiles are evaporated and the residue purified by normal phase MPLC (SiO2, heptane to heptane/EtOAc 3:1), giving 2-(4-formyl-3-methylphenyl)-2-methylpropanenitrile (1.89 g, 10.2 mmol, 73%) as a colorless liquid.

Workup

  1. customthe reaction is quenched with DMF (10 mL), volatiles
  2. customare evaporated
  3. customthe residue purified by normal phase MPLC (SiO2, heptane to heptane/EtOAc 3:1)

Sources & evidence

ORD record
ord-d948fc60311342a0977c183ac8a5ed2a
Source dataset
uspto-grants-2011_03
Patent number
US07906654B2

Reaction notes

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