Water → (S)-2,2,5,5-tetramethyl-1,3-dioxolane-4-carbaldehyde oxime

HRID 534063Notes

Reaction equation

HRID 534063 reaction equation
[CH3:1][C:2]1([CH3:11])[O:6][C@@H:5]([CH:7]=O)[C:4]([CH3:10])([CH3:9])[O:3]1.[OH2:12].Cl.[NH2:14]O.C([O-])([O-])=O.[Na+].[Na+]>CO>[CH3:1][C:2]1([CH3:11])[O:6][C@@H:5]([CH:7]=[N:14][OH:12])[C:4]([CH3:10])([CH3:9])[O:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 13227510(R)-2,2,5,5-Tetramethyl-1,3-dioxolane-4-carbaldehyde

Product 1

HCID 86644152(S)-2,2,5,5-tetramethyl-1,3-dioxolane-4-carbaldehyde oximeYield 74%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(R)-2,2,5,5-Tetramethyl-1,3-dioxolane-4-carbaldehyde (16 g, 101 mmol) [Burger, A. Synthesis 1989, (2) 93-97] was dissolved in 1:1 methanol:water (250 mL) and hydroxylamine hydrochloride (7.0 g, 101 mmol), and Na2CO3 (5.4 g, 51 mmol) was added. The reaction was stirred at ambient temperature for 2 hours. The methanol was partially removed in vacuo and the aqueous layer was extracted with CH2Cl2, dried, filtered and concentrated to afford (S)-2,2,5,5-tetramethyl-1,3-dioxolane-4-carbaldehyde oxime (13 g, 75 mmol, 74% yield) as an amber oil.

Workup

  1. customThe methanol was partially removed in vacuo
  2. extractionthe aqueous layer was extracted with CH2Cl2
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1a777672624342f6a5d7e9db96df68da
Source dataset
uspto-grants-2014_10
Patent number
US08853409B2

Reaction notes

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