Diisobutylaluminum hydride → HCID 86651524, compound

HRID 1912748Notes

Reaction equation

HRID 1912748 reaction equation
[C:1]([N:5]([OH:15])[C:6]([C:8]([CH3:14])([CH3:13])[C:9](OC)=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(C[AlH]CC(C)C)C>C(Cl)Cl>[C:1]([N:5]([OH:15])[C:6]([C:8]([CH3:14])([CH3:13])[CH:9]=[O:10])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 86651523HCID 86651523, compound

Product 1

HCID 86651524HCID 86651524, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of methyl 2-(tert-butyl-N-hydroxycarbamoyl)-isobutyrate (2.00 g) in dry CH2Cl2 (20 mL) at −78° C. under N2, 1M DIBAH in CH2Cl2 (17.14 mL) was added dropwise. The mixture was stirred at −78° C. for 3 hours and quenched by careful addition of MeOH (28 mL), Et2O (30 mL) and saturated aqueous solution of sodium potassium tartrate (30 mL). After 1 h the mixture was extracted three times with Et2O. The combined organic layers were washed with water, brine, dried over Na2SO4 and the solvent evaporated to dryness to give 2-(tert-butyl-N-hydroxycarbamoyl)-isobutyraldehyde (1.23 g, 71%). 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 10.02 (1H, s), 9.58 (1H, s), 1.38 (9H, s), 1.17 (6H, s).

Workup

  1. customquenched by careful addition of MeOH (28 mL), Et2O (30 mL) and saturated aqueous solution of sodium potassium tartrate (30 mL)
  2. extractionAfter 1 h the mixture was extracted three times with Et2O
  3. washThe combined organic layers were washed with water, brine
  4. dry with materialdried over Na2SO4
  5. customthe solvent evaporated to dryness

Sources & evidence

ORD record
ord-ccc8c2e4c6ad41298db6e46c5ae2164a
Source dataset
uspto-grants-2013_12
Patent number
US08609644B2

Reaction notes

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