Diisobutylaluminum hydride → HCID 11789327, compound

HRID 534138Notes

Reaction equation

HRID 534138 reaction equation
CON(C)[C:4]([C@:6]1([CH3:13])[CH2:10][O:9][C:8]([CH3:12])([CH3:11])[O:7]1)=[O:5].CC(C[AlH]CC(C)C)C>C1COCC1>[CH3:11][C:8]1([CH3:12])[O:7][C@:6]([CH3:13])([CH:4]=[O:5])[CH2:10][O:9]1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 86639851HCID 86639851, compound

Product 1

HCID 11789327HCID 11789327, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

(S)-N-methoxy-N,2,2,4-tetramethyl-1,3-dioxolane-4-carboxamide (23.1 g, 114 mmol) was dissolved in THF (600 mL) and cooled to −78° C. DIBAL-H (1M in toluene, 125 ml, 125 mmol) was added slowly through an addition funnel over about 15 minutes. The reaction was stirred for an additional 30 minutes at −78° C. and then quenched with saturated aqueous NH4Cl. The mixture was partitioned between EtOAc and water. The two layers were filtered through a silica plug and separated. The organic layer was dried over sodium sulfate, filtered and concentrated to afford (S)-2,2,4-trimethyl-1,3-dioxolane-4-carbaldehyde (16.4 g, 114 mmol, 100% yield).

Workup

  1. customquenched with saturated aqueous NH4Cl
  2. customThe mixture was partitioned between EtOAc and water
  3. filtrationThe two layers were filtered through a silica plug
  4. customseparated
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ac1c1259389c473ab70de2d6d574c8c5
Source dataset
uspto-grants-2014_10
Patent number
US08853409B2

Reaction notes

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