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

HRID 1948356ノート

反応式

HRID 1948356 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-453047f03436495e8381108bc7cd704a
出典データセット
uspto-grants-2013_03
特許番号
US08399489B2

反応ノート

読み込み中…