Water → HCID 390821, compound

HRID 534104Notes

Reaction equation

HRID 534104 reaction equation
[OH2:1].Cl.O[NH2:4].C(=O)([O-])[O-].[Na+].[Na+].[O:11]1[C:15]2([CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[O:14][CH2:13][C@@H:12]1[CH:21]=O>C1COCC1>[O:11]1[C:15]2([CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[O:14][CH2:13][C@@H:12]1[CH:21]=[N:4][OH:1]

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 10855919(2R)-1,4-Dioxaspiro[4.5]decane-2-carbaldehyde

Product 1

HCID 390821HCID 390821, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 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 larger portions and the reaction was stirred for 15 minutes. THF (700 mL) was added, followed by (R)-1,4-dioxaspiro[4.5]decane-2-carbaldehyde (125 g, 734 mmol) in 800 mL of THF. The reaction was stirred for 4 hours, then poured into a 4 L separatory funnel. The layers were separated and 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 were 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-3e2da751ff4d47ba8ebaacf71914ec6e
Source dataset
uspto-grants-2014_10
Patent number
US08853409B2

Reaction notes

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