Hydrochloric Acid → Ethyl 2-chloro-4-(hydroxymethyl)thiazole-5-carboxylate

HRID 1948356Notes

Reaction equation

HRID 1948356 reaction equation
[Si]([O:8][CH2:9][C:10]1[N:11]=[C:12]([Cl:20])[S:13][C:14]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16])(C(C)(C)C)(C)C.Cl>O1CCOCC1>[Cl:20][C:12]1[S:13][C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:10]([CH2:9][OH:8])[N:11]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68517702Ethyl 4-(((tert-butyldimethylsilyl)oxy)methyl)-2-chlorothiazole-5-carboxylate2×

Product 1

HCID 59208448Ethyl 2-chloro-4-(hydroxymethyl)thiazole-5-carboxylateYield 96.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 17.7 g (53 mmol) of ethyl 4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-chloro-1,3-thiazole-5-carboxylate (Intermediate 211) and 53 ml (53 mmol) of 1N HCl in dioxane was stirred at room temperature for 1 h. The mixture was extracted 3 times with EtOAc, which was dried (MgSO4) and concentrated to give 11.3 g of an orange oil. Purification by silica gel chromatography affords a solid. NMR (CDCl3): 1.2 (t, 3H), 3.1 (s, broad, 1H), 4.2 (q, 2H), 4.8 (s, 2H).

Workup

  1. extractionThe mixture was extracted 3 times with EtOAc, which
  2. dry with materialwas dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-453047f03436495e8381108bc7cd704a
Source dataset
uspto-grants-2013_03
Patent number
US08399489B2

Reaction notes

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