Diisobutylaluminum hydride → [1-(toluene-4-sulfonyl)-1H-pyrazol-4-yl]-methanol

HRID 559730

Reaction equation

HRID 559730 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([S:11]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)(=[O:13])=[O:12])[CH:10]=1)=O)C.CC(C[AlH]CC(C)C)C>C(Cl)Cl.C([O-])(O)=O.[Na+]>[C:17]1([CH3:20])[CH:16]=[CH:15][C:14]([S:11]([N:9]2[CH:10]=[C:6]([CH2:4][OH:3])[CH:7]=[N:8]2)(=[O:13])=[O:12])=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 216282771-(toluene-4-sulfonyl)-1H-pyrazole-4-carboxylic acid ethyl ester

Product 1

HCID 59278506[1-(toluene-4-sulfonyl)-1H-pyrazol-4-yl]-methanol

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

To a chilled (−78° C.) solution of 1-(toluene-4-sulfonyl)-1H-pyrazole-4-carboxylic acid ethyl ester (0.90 g, 3.06 mmol) in CH2Cl2 was added a 1 M solution of DIBAH (11.00 mL, 11.00 mmol) in CH2Cl2 dropwise. After 4 hours, the reaction was warmed to room temperature. After 8 hours, the mixture was diluted with saturated aqueous NaHCO3. After 2 hours, the solution was passed through the diatomaceous earth. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated in vacuo to afford the [1-(toluene-4-sulfonyl)-1H-pyrazol-4-yl]-methanol.

Workup

  1. waitAfter 8 hours
  2. waitAfter 2 hours
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bbb6d403d30d4f86bbc1092f1a921cd5
Source dataset
uspto-grants-2011_11
Patent number
US08063065B2

Linked notes

Loading…