Trimethylsilyl cyanide → Diethyl 5-(cyanomethyl)benzene-1,3-dioate

HRID 2243809노트

반응식

HRID 2243809 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].C[Si]([C:23]#[N:24])(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CC#N>[C:23]([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

5

반응물 3

HCID 82115Trimethylsilyl cyanideHCID 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 cyanide (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-cb6a261d7df54f2fa7935d953dd14bd1
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07678783B2

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