Diisobutylaluminumhydride → HCID 67935453, compound

HRID 986669Notes

Reaction equation

HRID 986669 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([C:7](=[CH2:12])C(OC)=O)[O:4][N:3]=1.[H-].C([Al+]CC(C)C)C(C)C.[CH3:23][OH:24].O>ClCCl.C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:6]=[C:5]([CH:7]=[CH:12][CH2:23][OH:24])[O:4][N:3]=1

Participants

6

Reactant 3

HCID 21225700DiisobutylaluminumhydrideHCID 22242641Methanol--water (1/1)HCID 57279117HCID 57279117, compound

Product 1

HCID 67935453HCID 67935453, compoundYield 67.6%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-70 °C

Procedure

A 8 g quantity of methyl 3-methyl-5-isoxazolylacrylate was dissolved in 150 ml of dichloromethane. To the solution was added dropwise with cooling at -70° C. or lower 100 ml of a 25 % solution of di-isobutyl aluminum hydride in toluene. After the addition, the reaction was effected for 30 minutes and then the excess of the reducing agent was decomposed with methanol-water. The organic layer was separated and dried over anhydrous sodium sulfate. After drying, the solvent was removed by distillation, giving 4.5 g of 3-methyl-5-isoxazolyl-allyl alcohol (Compound 4a) as an oil in a yield of 67.6 %. MS, m/e : 139 (M+).

Workup

  1. additionTo the solution was added dropwise
  2. additionAfter the addition
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. customAfter drying
  6. customthe solvent was removed by distillation

Sources & evidence

ORD record
ord-efac0fe07020410e92da028a6ce44fad
Source dataset
uspto-grants-1987_12
Patent number
US04714765

Reaction notes

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