Methanol → (5-Phenyl-1,3,4-thiadiazol-2-yl)methanol

HRID 1424351ノート

反応式

HRID 1424351 の反応式
[C:1]1([C:7]2[S:11][C:10]([C:12](OCC)=[O:13])=[N:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO.[BH4-].[Na+]>CC(O)=O>[C:1]1([C:7]2[S:11][C:10]([CH2:12][OH:13])=[N:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

5

反応物 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 67306900Ethyl 5-phenyl-1,3,4-thiadiazole-2-carboxylate

生成物 1

HCID 86700895(5-Phenyl-1,3,4-thiadiazol-2-yl)methanol

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

To a solution of ethyl 5-phenyl-1,3,4-thiadiazole-2-carboxylate (350 mgs, 1.494 mmol) in anhydrous methanol (5 mL, 124 mmol) was added NaBH4 (226 mgs, 5.98 mmol) at 0° C. The reaction mixture was stirred at ambient temperature for 16 h. AcOH (2 mL) was added and the reaction was concentrated to dryness. The residue was dissolved in EtOAc, brine and water and extracted with EtOAc (3×). The combined organic extracts were washed with sat. aqueous NaHCO3 and brine, and dried over anhydrous magnesium sulfate. After filtration and evaporation, the residue was triturated with ethyl ether to give the title material as a first crop (150 mgs, 52%). LC (Method B): 2.022 min, LCMS (APCI) calcd for C9H9N2OS [M+H]+ m/z 193.04. found 193.2. 1H NMR (CDCl3, 400 MHz) δ ppm: 7.92-8.03 (m, 2H), 7.44-7.59 (m, 3H), 5.14 (br. d, J=3.90 Hz, 2H), 2.63 (br. s., 1H).

後処理

  1. concentrationthe reaction was concentrated to dryness
  2. dissolutionThe residue was dissolved in EtOAc
  3. extractionbrine and water and extracted with EtOAc (3×)
  4. washThe combined organic extracts were washed with sat. aqueous NaHCO3 and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationAfter filtration and evaporation
  7. customthe residue was triturated with ethyl ether

出典と根拠

ORDレコード
ord-6fc6590859344ab2b4e497fffa532881
出典データセット
uspto-grants-2015_01
特許番号
US08927688B2

反応ノート

読み込み中…