Lithium Hydroxide → 2-Thiazolecarboxylic acid, 4-(1-methylethyl)-

HRID 471104ノート

反応式

HRID 471104 の反応式
[CH:1]([C:4]1[N:5]=[C:6]([C:9]([O:11]CC)=[O:10])[S:7][CH:8]=1)([CH3:3])[CH3:2].[OH-].[Li+]>CO.C1COCC1.O>[CH:1]([C:4]1[N:5]=[C:6]([C:9]([OH:11])=[O:10])[S:7][CH:8]=1)([CH3:3])[CH3:2]

参加物

6

反応物 2

HCID 3939Lithium HydroxideHCID 10821861Ethyl 4-isopropylthiazole-2-carboxylate

生成物 1

HCID 224993072-Thiazolecarboxylic acid, 4-(1-methylethyl)-

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
20 °C

実験手順

A solution of ethyl 4-isopropylthiazole-2-carboxylate (example 53, step a) (2.2 g) in a mixture of methanol (10 mL) and THF (20 mL) was treated with a solution of lithium hydroxide (0.264 g) in water (20 mL). The reaction mixture was stirred at 20° C. for 24 hours. The organic solvent was removed under reduced pressure and the remaining aqueous mixture was partitioned between ethyl acetate and water. The aqueous layer was acidified with 2M hydrochloric acid and extracted twice with ethyl acetate, the combined organics were washed with brine, dried over sodium sulphate, filtered and the solvent evaporated under reduced pressure. The crude product was triturated with cyclohexane to afford the subtitled compound. Yield 0.93 g.

後処理

  1. customThe organic solvent was removed under reduced pressure
  2. customthe remaining aqueous mixture was partitioned between ethyl acetate and water
  3. extractionextracted twice with ethyl acetate
  4. washthe combined organics were washed with brine
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. customthe solvent evaporated under reduced pressure
  8. customThe crude product was triturated with cyclohexane

出典と根拠

ORDレコード
ord-dbe70c69b87348afaec7547c0c4543db
出典データセット
uspto-grants-2014_01
特許番号
US08629271B2

反応ノート

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