Dabco → Benzyl cyanoformate

HRID 1459036Notes

Reaction equation

HRID 1459036 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[N:12]12CCN(CC1)C[CH2:13]2>>[C:13]([C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3])#[N:12]

Participants

3

Reactant 2

HCID 9237DabcoHCID 10387Benzyl chloroformate

Product 1

HCID 79660Benzyl cyanoformateYield 12,180.4%

Procedure

Benzyl chloroformate (13.7 g; 0.08 mol) and 1,4-diazabicyclo [2.2.2] octane (60 mg; 0.54 mmol) were added to a dry reaction vessel under a dry nitrogen atmosphere. Trimethylsilyl nitrile (8 g; 0.08 mol) was added dropwise over about 1 hr. The mixture was maintained at between 20°-30° C. until the reaction reached completion in about 3 hr. After distilling off the trimethylsilyl chloride, 10.6 g product was isolated as a clear liquid (bp 70-72/1 mm Hg.) Yield: 82%; purity 98% 1H-NMR: δ7.3,m(5H); δ5.26, s(2H); IR: 2250 cm-1 (CN), 1760 cm-1 (CO).

Workup

  1. temperatureThe mixture was maintained at between 20°-30° C. until the reaction
  2. customin about 3 hr
  3. distillationAfter distilling off the trimethylsilyl chloride

Sources & evidence

ORD record
ord-c2de903095a646aeb8246f11b1d32974
Source dataset
uspto-grants-1998_12
Patent number
US05852207

Reaction notes

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