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

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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]

참가 물질

반응물 3

HCID 8028Tetrahydrofuran

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

HCID 178418306HCID 178418306, 화합물

생성물 1

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

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온도: -78 °C

실험 절차

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.

후처리

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)

출처 및 근거

ORD 기록: ord-d948fc60311342a0977c183ac8a5ed2a
출처 데이터셋: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US07906654B2

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