Acetone → HCID 59771301, compound

HRID 1508101Notes

Reaction equation

HRID 1508101 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][CH:8]=[CH:9][N:10]=1)=[O:5])[CH3:2].C([O-])([O-])=O.[K+].[K+].[CH3:17][Si:18]([CH2:21][CH2:22][O:23][CH2:24]Cl)([CH3:20])[CH3:19].CC(C)=O>CCOC(C)=O>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:24][O:23][CH2:22][CH2:21][Si:18]([CH3:20])([CH3:19])[CH3:17])[CH:8]=[CH:9][N:10]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 549404ethyl 1H-imidazole-2-carboxylateHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl ether

Product 1

HCID 59771301HCID 59771301, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A flask charged with 1H-imidazole-2-carboxylic acid ethyl ester (1.03 g, 7.36 mmol), K2CO3 (2.00 g, 14.5 mmol), SEM-Cl (1.56 mL, 8.89 mmol), and 20 mL of acetone was stirred for 10 h at RT. The reaction was diluted with EtOAc (100 mL), washed with NaHCO3 (2×100 mL), brine (100 mL), and the organic layer dried over Na2SO4 and concentrated. The title compound was eluted from a 20-g SPE with 50% EtOAc/hexanes to give 1.50 g (76%) of a colorless oil. Mass spectrum (ESI, m/z): Calcd. for C12H22N3O3Si, 271.1 (M+H). found 271.1.

Workup

  1. washwashed with NaHCO3 (2×100 mL), brine (100 mL)
  2. dry with materialthe organic layer dried over Na2SO4
  3. concentrationconcentrated
  4. washThe title compound was eluted from a 20-g SPE with 50% EtOAc/hexanes

Sources & evidence

ORD record
ord-a0e979eab0054660b9db0f5083662dd5
Source dataset
uspto-grants-2015_12
Patent number
US09221797B2

Reaction notes

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