Ethyl Acetate → HCID 390821, compound

HRID 533994Notes

Reaction equation

HRID 533994 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]2)[O:4][CH2:3][C@@H:2]1[CH:11]=O.Cl.[OH:14][NH2:15].C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C>C1COCC1>[O:1]1[C:5]2([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]2)[O:4][CH2:3][C@@H:2]1[CH:11]=[N:15][OH:14]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 10855919(2R)-1,4-Dioxaspiro[4.5]decane-2-carbaldehyde

Product 1

HCID 390821HCID 390821, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-1,4-dioxaspiro[4.5]decane-2-carbaldehyde (9.0 g, 59.9 mmol) in THF (120 mL and 60 mL of water) was added hydroxyl amine hydrochloride (3.73 g, 52.9 mmol) and the reaction stirred until clear (10 minutes). Sodium carbonate (2.75 g, 25.9 mmol) was added and the reaction stirred overnight at ambient temperature. The reaction was poured into ethyl acetate (500 mL) and the layers were separated. The organics were washed with water (200 mL), brine (200 mL), dried over magnesium sulfate and concentrated in vacuo to yield (S)-1,4-dioxaspiro[4.5]decane-2-carbaldehyde oxime (9.08 g, 49 mmol, 92.7%).

Workup

  1. stirringthe reaction stirred overnight at ambient temperature
  2. customthe layers were separated
  3. washThe organics were washed with water (200 mL), brine (200 mL)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-142df55baa3f4aaebd47793c542ec9fe
Source dataset
uspto-grants-2014_10
Patent number
US08853409B2

Reaction notes

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