Diisobutylaluminum hydride → (6-Chloro-4-methoxypyridazin-3-YL)methanol

HRID 1244248Notes

Reaction equation

HRID 1244248 reaction equation
CC(C[AlH]CC(C)C)C.C[O:11][C:12]([C:14]1[N:15]=[N:16][C:17]([Cl:22])=[CH:18][C:19]=1[O:20][CH3:21])=O.[O-]S([O-])(=O)=O.[Na+].[Na+]>C(Cl)Cl>[Cl:22][C:17]1[N:16]=[N:15][C:14]([CH2:12][OH:11])=[C:19]([O:20][CH3:21])[CH:18]=1

Participants

5

Reactant 3

HCID 14487Diisobutylaluminum hydrideHCID 24436Sodium SulfateHCID 72210863HCID 72210863, compound

Product 1

HCID 21919279(6-Chloro-4-methoxypyridazin-3-YL)methanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

DIBAL (1N solution in THF, 4 mL) is added to a stirred solution of 6-chloro-4-methoxy-pyridazine-3-carboxylic acid methyl ester (182 mg, 0.9 mmol) in CH2Cl2 (10 mL) cooled to 0° C. The solution is stirred at 0° C. for 3 hours. Excess (Na2SO4).10H2O is then added and the mixture is stirred at room temperature for 45 minutes. The solid is washed with EtOAc, filtered, and the filtrate evaporated in vacuo. The resulting alcohol is used without further purification in the next step.

Workup

  1. stirringthe mixture is stirred at room temperature for 45 minutes
  2. washThe solid is washed with EtOAc
  3. filtrationfiltered
  4. customthe filtrate evaporated in vacuo
  5. customThe resulting alcohol is used without further purification in the next step

Sources & evidence

ORD record
ord-3283816b609a4b74a56b33c315700d00
Source dataset
uspto-grants-2006_10
Patent number
US07122546B2

Reaction notes

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