Diisobutylaluminum hydride → HCID 54504767, compound

HRID 850627Notes

Reaction equation

HRID 850627 reaction equation
[C:1]([O:5][C:6](=[O:25])[N:7]([CH2:15][CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([Br:24])[N:19]=1)[CH2:8][C:9](=[O:14])N(OC)C)([CH3:4])([CH3:3])[CH3:2].CC(C[AlH]CC(C)C)C>C1COCC1>[C:1]([O:5][C:6](=[O:25])[N:7]([CH2:15][CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([Br:24])[N:19]=1)[CH2:8][CH:9]=[O:14])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 54034496HCID 54034496, compound

Product 1

HCID 54504767HCID 54504767, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 20-7 (14.9 g, 35.7 mmol) and THF (100 ml) at -78° C. was added DIBAL (1.0M/hexanes, 53.6 ml, 53.6 mmol) dropwise over 20 minutes. After 1 h, the mixture was warmed to RT and quenched by the careful addition of 20 mL MeOH. 200 ml of 1.0 M Rochelle's salt was then added followed by the removal of the cooling bath. The mixture was stirred for 1.0 hour and then diluted with Et2O. After another 30 minutes of stirring, the organic portion was separated and dried over MgSO4. Evaporative removal of the solvent gave the crude aldehyde 20-8 as a colorless oil.

Workup

  1. customquenched by the careful addition of 20 mL MeOH
  2. addition200 ml of 1.0 M Rochelle's salt was then added
  3. customfollowed by the removal of the cooling bath
  4. additiondiluted with Et2O
  5. stirringAfter another 30 minutes of stirring
  6. customthe organic portion was separated
  7. dry with materialdried over MgSO4
  8. customEvaporative removal of the solvent

Sources & evidence

ORD record
ord-30c87a488b554f7d8c133d3b515f4bda
Source dataset
uspto-grants-2000_01
Patent number
US06017926

Reaction notes

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