Hydrochloric Acid → 5-Hydroxymethyl-3-(2-methyl(ethyl)carbonylamino)pyrazole

HRID 1018501Notes

Reaction equation

HRID 1018501 reaction equation
C([CH2:4][C:5]1[NH:9][N:8]=[C:7]([NH:10][C:11]([CH2:13][CH2:14][CH3:15])=[O:12])[CH:6]=1)(O)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].Cl.C1C[O:26]CC1>>[OH:26][CH2:4][C:5]1[NH:9][N:8]=[C:7]([NH:10][C:11]([CH2:13][CH2:14][CH3:15])=[O:12])[CH:6]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran2×HCID 21226445Aluminium lithium hydrideHCID 86587208HCID 86587208, compound

Product 1

HCID 867586095-Hydroxymethyl-3-(2-methyl(ethyl)carbonylamino)pyrazoleYield 15%

Conditions

Temperature
0 °C

Procedure

A solution of 787 mg of crude XII in 10 ml of dry THF was cooled to 0° C. in an ice bath. To this mixture was added 14 ml of 1 M LiAlH4 in THF while maintaining the temperature at 0° C. The reaction was allowed to stir at 0° C. for 6.5 hours at which point the solution was poured over 100 g of crushed ice. Once the ice had melted, the solution was brought to pH 7 by addition of HCl. The water layer was filtered to remove aluminum salts and the filtrate was extracted three times with 75 ml of ethyl acetate. The organic layer was collected, dried over MgSO4 and evaporated to an orange solid. The solid was purified on silica gel to give 79 mg of the alcohol (15%).

Workup

  1. filtrationThe water layer was filtered
  2. customto remove aluminum salts
  3. extractionthe filtrate was extracted three times with 75 ml of ethyl acetate
  4. customThe organic layer was collected
  5. dry with materialdried over MgSO4
  6. customevaporated to an orange solid
  7. customThe solid was purified on silica gel

Sources & evidence

ORD record
ord-c3a0b0d38d264d9a915f36a8aa210a4e
Source dataset
uspto-grants-2002_11
Patent number
US06482842B2

Reaction notes

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