Tetrahydrofuran → (R)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde oxime

HRID 534117Notes

Reaction equation

HRID 534117 reaction equation
[CH3:1][C:2]1([CH3:10])[O:6][C@H:5]([C:7](=O)C)[CH2:4][O:3]1.C1COCC1.Cl.[NH2:17][OH:18].C([O-])([O-])=O.[Na+].[Na+]>O>[CH3:1][C:2]1([CH3:10])[O:6][C@H:5]([CH:7]=[N:17][OH:18])[CH2:4][O:3]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 10340Sodium CarbonateHCID 188603Ethanone, 1-(2,2-dimethyl-1,3-dioxolan-4-yl)-, (S)-HCID 443297Hydroxyamine hydrochloride

Product 1

HCID 86644159(R)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde oximeYield 97.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of (S)-1-(2,2-dimethyl-1,3-dioxolan-4-yl)ethanone (10.5 g, 72.8 mmol) in 150 (mL) THF: 60 mL water was added hydroxylamine hydrochloride (5.06 g, 72.8 mmol), and the reaction was stirred for 20 minutes. Na2CO3 (3.78 g, 35.7 mmol) was added and the reaction was stirred overnight. The reaction was extracted with ethyl acetate, washed with water and brine, dried over MgSO4, filtered and concentrated to afford (R)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde oxime (10.3 g, 71.0 mmol, 97.4% yield).

Workup

  1. stirringthe reaction was stirred overnight
  2. extractionThe reaction was extracted with ethyl acetate
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-bdd130174c6b43cbba5f2f48a1bc960e
Source dataset
uspto-grants-2014_10
Patent number
US08853409B2

Reaction notes

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