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

HRID 471104

반응식

HRID 471104 반응식
[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]

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
20 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-dbe70c69b87348afaec7547c0c4543db
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629271B2

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