Ammonium Chloride → HCID 11423659, compound

HRID 534128Notes

Reaction equation

HRID 534128 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-f6d2f6a2ecbe4cf5a14f13aa4c9ef879
Source dataset
uspto-grants-2014_10
Patent number
US08853409B2

Reaction notes

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