Tetrabutylammonium Fluoride → Diethyl 5-(cyanomethyl)benzene-1,3-dioate

HRID 2261884노트

반응식

HRID 2261884 반응식
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[C:10]([CH2:12]Br)[CH:9]=[C:8]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:7]=1)=[O:5])[CH3:2].[F-].[CH2:20]([N+:24](CCCC)(CCCC)CCCC)CCC>CC#N>[C:20]([CH2:12][C:10]1[CH:9]=[C:8]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:7]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH:11]=1)#[N:24]

참가 물질

4

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 10935954Diethyl 5-(Bromomethyl)isophthalate

생성물 1

HCID 59709094Diethyl 5-(cyanomethyl)benzene-1,3-dioate

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of diethyl-5-(bromomethyl)benzene-1,3-dioate (1.9 g, 6.0 mmol) in 69 mL MeCN was added trimethylsilyl cyamide (1.2 mL, 9.0 mmol) and tetrabutylammonium fluoride (1M in THF, 9.0 mL, 9.0 mmol). The reaction was stirred for 0.5 h and concentrated. Flash chromatography (silica gel, 0-30% EtOAc/hexanes) gave diethyl 5-(cyanomethyl)benzene-1,3-dioate. 1H NMR (400 MHz, CDCl3) δ 8.65 (s, 1H), 8.20 (app t, J=0.7 Hz, 2H), 4.43 (q, J=7.1 Hz, 4H), 3.86 (s, 2H), 1.43 (t, J=7.1 Hz, 6H).

후처리

  1. concentrationconcentrated

출처 및 근거

ORD 기록
ord-64814dff184f4619a9946bad92e2a74d
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07847100B2

반응 노트

불러오는 중…