Ethyl Acetate → HCID 390821, compound

HRID 1511003Notes

Reaction equation

HRID 1511003 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, 52.9 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-0247377e7a6d4e8b98d09e16ee2164e3
Source dataset
uspto-grants-2012_07
Patent number
US08212045B2

Reaction notes

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