Ethyl orthoformate → 1-diethoxymethyl-1H-indole-3-carbonitrile

반응식

[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]#[N:11])=[CH:2]1.[CH2:12]([O:14][CH:15](OCC)[O:16][CH2:17][CH3:18])[CH3:13]>>[CH2:12]([O:14][CH:15]([O:16][CH2:17][CH3:18])[N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]#[N:11])=[CH:2]1)[CH3:13]

참가 물질

반응물 2

HCID 31214Ethyl orthoformate

HCID 2302823-Cyanoindole

생성물 1

HCID 592776081-diethoxymethyl-1H-indole-3-carbonitrile수율 86%

실험 절차

1H-Indole-3-carbonitrile (5.07 g, 35.7 mmol) was heated with triethylorthoformate (60 mL) in a pressure vessel at 160° C. for 3 d. Upon cooling, the solvent was evaporated and the residue was submitted to chromatography (20% ether in hexanes) to afford the title compound (7.46 g, 86%). NMR (300 MHz, CDCl3, 8): 7.92 (s, 1H), 7.76 (m, 1H), 7.62 (m, 1H), 7.32 (m, 2H), 6.23 (s, 1H), 3.63 (m, 4H), 1.23 (t, J=7.2 Hz, 6H).

후처리

temperatureUpon cooling
customthe solvent was evaporated

출처 및 근거

ORD 기록: ord-701ff3b6083848988fde0544d0242b4e
출처 데이터셋: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US08450307B2

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