Potassium Hydroxide → (4-Phenyl-1,3-thiazol-2-yl)methanol

HRID 1397292ノート

反応式

HRID 1397292 の反応式
[OH-].[K+].[C:3]1([C:9]2[N:10]=[C:11]([CH2:14][O:15]C(=O)C3C=CC=CC=3)[S:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(O)(=O)C1C=CC=CC=1>CCO>[C:3]1([C:9]2[N:10]=[C:11]([CH2:14][OH:15])[S:12][CH:13]=2)[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

参加物

4

反応物 2

HCID 14797Potassium HydroxideHCID 67348234Benzoic acid (4-phenylthiazol-2-yl)methyl benzoate

生成物 1

HCID 698895(4-Phenyl-1,3-thiazol-2-yl)methanol収率 87.4%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

Potassium hydroxide (1.06 g, 18.84 mmol) was added to an ice cooled solution of benzoic acid (4-phenylthiazol-2-yl)methyl benzoate (3.71 g, 12.56 mmol) in EtOH (40 mL). The reaction mixture was slowly warmed to room temperature and allowed to stir for 1 h. The reaction mixture was concentrated under reduced pressure and then diluted with water. The organic product was extracted with EtOAc, washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude product was purified by column chromatography (silica 60-120 mesh, eluant 10% EtOAc in petroleum ether) to get the pure (4-phenylthiazol-2-yl)methanol (2.1 g, yield 87%). 1H NMR (400 MHz, CDCl3) δ 7.89-7.87 (m, 2H), 7.46-7.41 (m, 3H), 7.37-7.33 (m, 1H), 5.01 (s, 2H). MS (ESI) m/z: Calculated for C10H9NOS: 191.04. found: 192.2 (M+H)+.

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiondiluted with water
  3. extractionThe organic product was extracted with EtOAc
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by column chromatography (silica 60-120 mesh, eluant 10% EtOAc in petroleum ether)

出典と根拠

ORDレコード
ord-0c337bf78f3645ac8b32942228b81131
出典データセット
uspto-grants-2014_12
特許番号
US08901156B2

反応ノート

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