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

HRID 899458Notes

Reaction equation

HRID 899458 reaction equation
[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]

Participants

5

Reactant 3

HCID 82115Trimethylsilyl cyanideHCID 2724141Tetrabutylammonium FluorideHCID 10935954Diethyl 5-(Bromomethyl)isophthalate

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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).

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-a1ac7e222b074903a47ab17a764ee50a
Source dataset
uspto-grants-2008_04
Patent number
US07354942B2

Reaction notes

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