Diethyl Ether → (4,6-Dihydropyrazolo[1,5-c]thiazol-2-yl)methanol

HRID 2216574노트

반응식

HRID 2216574 반응식
[Li+].[BH4-].CCOCC.C([O:10][C:11]([C:13]1[CH:20]=[C:19]2[N:15]([CH2:16][S:17][CH2:18]2)[N:14]=1)=O)C>CO>[N:14]1[N:15]2[C:19]([CH2:18][S:17][CH2:16]2)=[CH:20][C:13]=1[CH2:11][OH:10]

참가 물질

5

반응물 3

HCID 3283Diethyl EtherHCID 4148881Lithium borohydrideHCID 21057705Ethyl 4H,6H-pyrazolo[1,5-c]thiazole-2-carboxylate

생성물 1

HCID 21941435(4,6-Dihydropyrazolo[1,5-c]thiazol-2-yl)methanol

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

LiBH4 (cont. 90%) (459 mg) was added to the ether (126 mL) solution of 4H-5-thia-1,6a-diazapentalen-2-carboxylic acid ethylester (2.5 g) and MeOH (0.77 mL) under a nitrogen atmosphere at room temperature, then refluxed for 1.5 h. The mixture was quenched with 1 mol/L HCl (25 mL) and stirred for 1 h at room temperature. The mixture was neutralized by saturated sodium hydrogen carbonate solution and separated. The aqueous layer was extracted with dichloromethane (10×25 mL). The organic layer was dried (MgSO4) and filtered. The filtrate was concentrated under reduced pressure. The residue was applied to silica gel column chromatography, then the column was eluted with AcOEt. The titled compound was obtained as a pale yellow solid (1.7 g, 87.9%).

후처리

  1. temperaturerefluxed for 1.5 h
  2. customThe mixture was quenched with 1 mol/L HCl (25 mL)
  3. customseparated
  4. extractionThe aqueous layer was extracted with dichloromethane (10×25 mL)
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. washthe column was eluted with AcOEt

출처 및 근거

ORD 기록
ord-d25be93f0c964029b6b8d7c88c5e30bc
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07112582B2

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