Diethyl Ether → (4H,6H-Pyrazolo[1,5-c][1,3]thiazol-2-yl)methanol

HRID 2216574Notes

Reaction equation

HRID 2216574 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

HCID 21941435(4H,6H-Pyrazolo[1,5-c][1,3]thiazol-2-yl)methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-d25be93f0c964029b6b8d7c88c5e30bc
Source dataset
uspto-grants-2006_09
Patent number
US07112582B2

Reaction notes

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