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

HRID 625109노트

반응식

HRID 625109 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-6f19575b8f9f415493bffb0b1802cf16
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09303065B2

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