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

HRID 899458노트

반응식

HRID 899458 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-a1ac7e222b074903a47ab17a764ee50a
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07354942B2

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