Ethyl cyanoformate → 5-Methyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid ethyl ester

HRID 1190164Notes

Reaction equation

[CH3:1][C:2]1[N:6]([CH2:7][O:8][CH2:9][CH2:10][Si:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=[N:4][CH:3]=1.[Li]CCCC.C([C:22]([O:24][CH2:25][CH3:26])=[O:23])#N>C1COCC1.CCOC(C)=O>[CH2:25]([O:24][C:22]([C:5]1[N:6]([CH2:7][O:8][CH2:9][CH2:10][Si:11]([CH3:13])([CH3:12])[CH3:14])[C:2]([CH3:1])=[CH:3][N:4]=1)=[O:23])[CH3:26]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 5-methyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole (0.320 g, 1.50 mmol) in 5 mL of THF at −78° C. was added n-BuLi (0.80 mL, 1.60 mmol, 2 M in cyclohexane) and the mixture was allowed to attain RT and stirred for 30 min. The mixture was cooled to −78° C. and ethyl cyanoformate (0.160 g, 1.65 mmol) was added and the mixture allowed to stir for 10 h at RT. The reaction was diluted with 15 mL of EtOAc and washed with NaHCO3 (2×15 mL) and brine (15 mL). The title compound was eluted from a 20-g SPE with 50% EtOAc/hexanes to give 0.160 g (38%) of a light brown oil: Mass spectrum (ESI, m/z): Calcd. for C13H24N2O3Si, 285.2 (M+H). found 284.9.

Workup

customto attain RT
stirringto stir for 10 h at RT
washwashed with NaHCO3 (2×15 mL) and brine (15 mL)
washThe title compound was eluted from a 20-g SPE with 50% EtOAc/hexanes

Sources & evidence

ORD record: ord-0eda398906ee40b7bed797c1b6f4894c
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08674100B2

Reaction notes

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