Sodium Carbonate → HCID 86644166, compound

HRID 1511158Notes

Reaction equation

HRID 1511158 reaction equation
[CH3:1][C:2]1([CH3:10])[O:6][C@:5]([CH3:9])([CH:7]=O)[CH2:4][O:3]1.Cl.[NH2:12][OH:13].C([O-])([O-])=O.[Na+].[Na+]>O.CO>[CH3:1][C:2]1([CH3:10])[O:6][C@:5]([CH3:9])([CH:7]=[N:12][OH:13])[CH2:4][O:3]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 11789327HCID 11789327, compound

Product 1

HCID 86644166HCID 86644166, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

(S)-2,2,4-trimethyl-1,3-dioxolane-4-carbaldehyde (5.8 g, 40 mmol) was dissolved in 1:1 methanol water (100 mL) and hydroxylamine hydrochloride (2.8 g, 40 mmol) and Na2CO3 (2.1 g, 20 mmol). The reaction was stirred at ambient temperature overnight, then concentrated in vacuo. The aqueous layer was extracted with CH2Cl2, and the organic layer was dried over sodium sulfate, filtered and concentrated to afford (R)-2,2,4-trimethyl-1,3-dioxolane-4-carbaldehyde oxime (4.8 g, 30 mmol, 75% yield).

Workup

  1. concentrationconcentrated in vacuo
  2. extractionThe aqueous layer was extracted with CH2Cl2
  3. dry with materialthe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-da11951f95bd4a3dae53e46d5b9e9c1b
Source dataset
uspto-grants-2012_07
Patent number
US08212045B2

Reaction notes

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