Sodium Carbonate → HCID 390821, compound

HRID 1511044Notes

Reaction equation

HRID 1511044 reaction equation
Cl.[OH:2][NH2:3].C(=O)([O-])[O-].[Na+].[Na+].[O:10]1[C:14]2([CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[O:13][CH2:12][C@@H:11]1[CH:20]=O>O.C1COCC1>[O:10]1[C:14]2([CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[O:13][CH2:12][C@@H:11]1[CH:20]=[N:3][OH:2]

Participants

6

Reactant 3

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

Product 1

HCID 390821HCID 390821, compoundYield 99.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

In 1000 mL of DI water was added hydroxyl amine hydrochloride (51.0 g, 734 mmol) and the reaction was stirred for 5 minutes. Sodium carbonate (38.1 g, 360 mmol) was added in 3 large portions and the reaction was stirred for 15 minutes. THF (700 mL) was added to the reaction and (R)-1,4-dioxaspiro[4.5]decane-2-carbaldehyde (125 g, 734 mmol) was added in 1 portion in 800 mL of THF. The reaction was stirred for 4 hours, then poured into a 4 L separatory funnel and the layers separated. The aqueous layer was extracted twice with MTBE (about 3000 mL total). The combined organic layers were washed with water (700 mL) and brine (300 mL), dried over MgSO4 and concentrated in vacuo to afford (S)-1,4-dioxaspiro[4.5]decane-2-carbaldehyde oxime (135 g, 99%) as a clear viscous oil.

Workup

  1. stirringthe reaction was stirred for 15 minutes
  2. stirringThe reaction was stirred for 4 hours
  3. additionpoured into a 4 L separatory funnel
  4. customthe layers separated
  5. extractionThe aqueous layer was extracted twice with MTBE (about 3000 mL total)
  6. washThe combined organic layers were washed with water (700 mL) and brine (300 mL)
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-60e6ab924ff84ac49edfcdd477b0e442
Source dataset
uspto-grants-2012_07
Patent number
US08212045B2

Reaction notes

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