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

反応式

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]

参加物

反応物 3

HCID 8028Tetrahydrofuran

HCID 582984722-(4-Bromo-3-methylphenyl)-2-methylpropanenitrile

HCID 178418306HCID 178418306、化合物

生成物 1

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

反応条件

温度: -78 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード: ord-d948fc60311342a0977c183ac8a5ed2a
出典データセット: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US07906654B2

反応ノート

読み込み中…

参加物