Ammonium Chloride → HCID 11423659, compound

HRID 1511147Notes

Reaction equation

HRID 1511147 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].[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH4+].[Cl-]>C1COCC1>[CH3:11][C:8]1([CH3:12])[O:7][C@@:6]([CH3:13])([CH:4]=[O:5])[CH2:10][O:9]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 86644162HCID 86644162, compound

Product 1

HCID 11423659HCID 11423659, compoundYield 61.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

(R)-N-methoxy-N,2,2,4-tetramethyl-1,3-dioxolane-4-carboxamide (22.9 g, 113 mmol) was dissolved in THF (500 mL) and cooled to −78° C. 1M LAH (124 ml, 124 mmol) was added slowly through an addition funnel over about 30 minutes. The reaction was stirred for another 30 minutes, a saturated aqueous NH4Cl was added (125 mL) and the reaction was allowed to warm to ambient temperature. After filtration, the slurry mixture was washed several times with EtOAc, and concentrated to afford crude (R)-2,2,4-trimethyl-1,3-dioxolane-4-carbaldehyde (10 g, 69.4 mmol, 61.6% yield) which was taken on to next reaction without further purification.

Workup

  1. temperatureto warm to ambient temperature
  2. filtrationAfter filtration
  3. washthe slurry mixture was washed several times with EtOAc
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a785ee17295b4101b0559d7ed54b005c
Source dataset
uspto-grants-2012_07
Patent number
US08212045B2

Reaction notes

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