Aluminium lithium hydride → (4-Ethylthiazol-5-yl)methanol

HRID 630268ノート

反応式

HRID 630268 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([C:9]1[N:10]=[CH:11][S:12][C:13]=1[C:14](OCC)=[O:15])[CH3:8]>C1COCC1>[CH2:7]([C:9]1[N:10]=[CH:11][S:12][C:13]=1[CH2:14][OH:15])[CH3:8]

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 53421078Ethyl 4-ethylthiazole-5-carboxylate

生成物 1

HCID 59589347(4-Ethylthiazol-5-yl)methanol収率 71.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

To a 0° C. mixture of lithium aluminum hydride (800 mg, 21.0 mmol) in anhydrous THF (30 mL) was slowly added a solution of ethyl 4-ethyl-1,3-thiazole-5-carboxylate (1.91 g, 10.3 mmol) in anhydrous THF (50 mL). The reaction mixture was stirred at 0° C. for 1.5 hours. The reaction was quenched with 5 N NaOH. Water (150 mL) and EtOAc (150 mL) were added. The mixture was stirred for 30 minutes. The solid material was removed by filtration. The organic layer was recovered. The aqueous layer was extracted with EtOAc (1×100 mL). The combined organic extracts were back extracted with brine (2×200 mL), dried over MgSO4, filtered, evaporated, and dried in vacuo, affording (4-ethyl-1,3-thiazol-5-yl)methanol (1.05 g, 71% yield). The product was used without further purification.

後処理

  1. customThe reaction was quenched with 5 N NaOH
  2. additionWater (150 mL) and EtOAc (150 mL) were added
  3. stirringThe mixture was stirred for 30 minutes
  4. customThe solid material was removed by filtration
  5. customThe organic layer was recovered
  6. extractionThe aqueous layer was extracted with EtOAc (1×100 mL)
  7. extractionThe combined organic extracts were back extracted with brine (2×200 mL)
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customevaporated
  11. customdried in vacuo

出典と根拠

ORDレコード
ord-c5163d10285f4341876f54d05848ab5f
出典データセット
uspto-grants-2016_04
特許番号
US09315521B2

反応ノート

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