Trimethylsilyldiazomethane → Methyl 2-(4-chlorophenyl)-4-[(methoxymethoxy)methyl]-1,3-oxazole-5-carboxylate

HRID 508169Notes

Reaction equation

HRID 508169 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([C:18]([OH:20])=[O:19])=[C:11]([CH2:13][O:14][CH2:15][O:16][CH3:17])[N:12]=2)=[CH:4][CH:3]=1.[CH3:21][Si](C=[N+]=[N-])(C)C>C1(C)C=CC=CC=1.CO.CCCCCC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([C:18]([O:20][CH3:21])=[O:19])=[C:11]([CH2:13][O:14][CH2:15][O:16][CH3:17])[N:12]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 582843362-(4-Chlorophenyl)-4-[(methoxymethoxy)methyl]-1,3-oxazole-5-carboxylic acid

Product 1

HCID 58284400Methyl 2-(4-chlorophenyl)-4-[(methoxymethoxy)methyl]-1,3-oxazole-5-carboxylate

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

138 mg (0.52 mmol) of the compound from Example 42A are dissolved in 3 ml toluene and 2.5 ml of methanol. 0.4 ml (0.79 mmol) of a 2 M solution of trimethylsilyldiazomethane in hexane is then added dropwise. The mixture is stirred at RT for 10 min and the solvent is then removed on a rotary evaporator. The residue is used without further purification in the subsequent reaction.

Workup

  1. customthe solvent is then removed on a rotary evaporator
  2. customThe residue is used without further purification in the subsequent reaction

Sources & evidence

ORD record
ord-5f1b0992f6934014a33833ea9404f324
Source dataset
uspto-grants-2015_08
Patent number
US09095582B2

Reaction notes

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