Methanol → HCID 68486406, compound

HRID 1875116Notes

Reaction equation

HRID 1875116 reaction equation
[OH-].[Li+].[CH3:3][C:4]1[N:5]=[C:6]([CH:22]([CH3:24])[CH3:23])[N:7]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[C:8]=1[C:9]([O:11]CC)=[O:10].CO.OP(O)(O)=O>C1COCC1>[CH3:3][C:4]1[N:5]=[C:6]([CH:22]([CH3:24])[CH3:23])[N:7]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:19])([CH3:21])[CH3:20])[C:8]=1[C:9]([OH:11])=[O:10]

Participants

6

Reactant 4

HCID 887MethanolHCID 1004Phosphoric AcidHCID 3939Lithium HydroxideHCID 68486336HCID 68486336, compound

Product 1

HCID 68486406HCID 68486406, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

Lithium hydroxide (2 mL, 2 mmol, 1 M in H2O) was added to a solution of ethyl 4-methyl-2-(1-methylethyl)-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxylate (133 mg, 0.41 mmol) in THF:MeOH (6 mL/2 mL). The reaction mixture was heated at 40° C. and stirred overnight. The mixture was then acidified by H3PO4 (1N), extracted with 10% MeOH in CHCl3 and the organic layer was dried over sodium sulfate. The solvent was evaporated and dried in vacuo to give the title compound (122 mg, >99%) as a yellow gel which was directly used in the next step without purification. LCMS: m/z 299 (M+1).

Workup

  1. extractionextracted with 10% MeOH in CHCl3
  2. dry with materialthe organic layer was dried over sodium sulfate
  3. customThe solvent was evaporated
  4. customdried in vacuo

Sources & evidence

ORD record
ord-d58be7624307484080679492ac3d9268
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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