Diisobutylaluminumhydride → HCID 57899279, compound

HRID 549380Notes

Reaction equation

HRID 549380 reaction equation
C([O:3][C:4](=O)[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[C:7]1[CH3:15])C.[H-].C([Al+]CC(C)C)C(C)C>C(COC)OC.ClCCl.C1CCCCC1>[CH3:15][C:7]1[N:6]([CH2:5][CH:4]=[O:3])[C:14]2[C:9]([CH:8]=1)=[CH:10][CH:11]=[CH:12][CH:13]=2

Participants

5

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 28881253HCID 28881253, compound

Product 1

HCID 57899279HCID 57899279, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 8078CyclohexaneSolventHCID 86634710Dimethoxyethane methylene chlorideSolvent

Conditions

Temperature
-70 °C

Procedure

A solution of (2-methyl-indol-1-yl)-acetic acid ethyl ester (400 mL, 1.97 mmol) in dimethoxyethane-dichloromethane (1:1, 30 mL) was cooled to −70° C. and treated with a solution of diisobutyl aluminum hydride in cyclohexane (3.9 mL, 1.0 M). The reaction was stirred at −70° C. for 4 h, quenched with an aqueous solution of hydrochloric acid (80 mL, 1 N) and extracted with ethyl acetate. The organic layers were combined, dried over sodium sulfate, filtered and concentrated, and the residue was purified to give (2-methyl-indol-1-yl)-acetaldehyde (234 mg, 75% yield). LCMS (m/z): 206.1 (M+1).

Workup

  1. customquenched with an aqueous solution of hydrochloric acid (80 mL, 1 N)
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customthe residue was purified

Sources & evidence

ORD record
ord-6737e4f8f9584753a7f4aa929baa9104
Source dataset
uspto-grants-2011_05
Patent number
US07943652B2

Reaction notes

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