Methanol → Methyl 2-methoxy-5-phenylthiazole-4-carboxylate

HRID 383925Notes

Reaction equation

HRID 383925 reaction equation
[H-].[Na+].Cl[C:4]1[S:5][C:6]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:7]([C:9]([O:11][CH2:12]C)=[O:10])[N:8]=1.[OH2:20].[CH3:21]O>>[CH3:21][O:20][C:4]1[S:5][C:6]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:7]([C:9]([O:11][CH3:12])=[O:10])[N:8]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 24758Sodium hydrideHCID 59291332Ethyl 2-chloro-5-phenylthiazole-4-carboxylate

Product 1

HCID 12821998Methyl 2-methoxy-5-phenylthiazole-4-carboxylate

Conditions

Temperature
70 °C

Procedure

To a solution of 60% oily NaH in MeOH was added ethyl 2-chloro-5-phenylthiazole-4-carboxylate, followed by stirring at 70° C. for 1 hour. To the reaction mixture was added water, followed by extraction with EtOAc. The organic layer was washed with water and brine in this order, dried over MgSO4, and then concentrated under reduced pressure. The residue was purified by medium-pressure preparative liquid chromatography (silica gel, YAMAZEN YFLC WPrep2XY, CHCl3:MeOH) to obtain methyl 2-methoxy-5-phenylthiazole-4-carboxylate as a white solid.

Workup

  1. extractionfollowed by extraction with EtOAc
  2. washThe organic layer was washed with water and brine in this order
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by medium-pressure preparative liquid chromatography (silica gel, YAMAZEN YFLC WPrep2XY, CHCl3:MeOH)

Sources & evidence

ORD record
ord-1f0ac69bc0b4461caac4267e68d194dd
Source dataset
uspto-grants-2013_02
Patent number
US08367696B2

Reaction notes

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