Diisobutylaluminum hydride → HCID 21087551, compound

HRID 348516Notes

Reaction equation

HRID 348516 reaction equation
[CH2:1]([N:3]1[N:7]=[C:6]2[CH:8]=[CH:9][C:10]([C:12](OCC)=[O:13])=[CH:11][C:5]2=[N:4]1)[CH3:2].CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[CH2:1]([N:3]1[N:7]=[C:6]2[CH:8]=[CH:9][C:10]([CH2:12][OH:13])=[CH:11][C:5]2=[N:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydride3×HCID 21087567HCID 21087567, compound

Product 1

HCID 21087551HCID 21087551, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 2-ethylbenzotriazole-5-carboxylate (0.7 g, 3.06 mmol) was dissolved in dry toluene (10 mL) and cooled to 0° C. under nitrogen. A solution of DIBAL-H (1.5M in toluene, 3 mL, 4.5 mmol) was then added dropwise to the cooled solution over 15 minutes. The reaction was stirred at 0° C. for one hour when further DIBAL-H (1.5 mL, 2.25 mmol) was added. A further aliquot of DIBAL-H (0.75 mL, 1.12 mmol) was added after 2 hours and the reaction was stirred for further 30 min. The reaction was quenched by addition of a saturated solution of sodium potassium tartrate, diluted with water and extracted with AcOEt. The organic layer was dried over sodium sulfate to give a crude oil (440 mg) which was used directly in the following step.

Workup

  1. additionwas added
  2. customThe reaction was quenched by addition of a saturated solution of sodium potassium tartrate
  3. additiondiluted with water
  4. extractionextracted with AcOEt
  5. dry with materialThe organic layer was dried over sodium sulfate

Sources & evidence

ORD record
ord-49a608563d2a43f9848494c7aca8e859
Source dataset
uspto-grants-2007_02
Patent number
US07176322B2

Reaction notes

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