Acetone → 1-Oxa-2-aza-spiro[4.5]dec-2-ene-3-carbaldehyde

HRID 1518151Notes

Reaction equation

HRID 1518151 reaction equation
C[O:2][CH:3](OC)[C:4]1[CH2:8][C:7]2([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[O:6][N:5]=1.CC(C)=O>O>[O:6]1[C:7]2([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH2:8][C:4]([CH:3]=[O:2])=[N:5]1

Participants

4

Reactant 2

HCID 180AcetoneHCID 592800713-Dimethoxymethyl-1-oxa-2-aza-spiro[4.5]dec-2-ene

Product 1

HCID 592801071-Oxa-2-aza-spiro[4.5]dec-2-ene-3-carbaldehydeYield 54%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-Dimethoxymethyl-1-oxa-2-aza-spiro[4.5]dec-2-ene (1.06 g, 4.97 mmol, as prepared in the previous step) was placed in a 50 mL round-bottom flask equipped with a stir bar. Acetone (20 mL), water (0.3 mL), and Amberlyst-15 resin (200 mg) were added. The mixture was stirred at rt for 24 h. The solids were removed by filtration and rinsed with acetone (20 mL), and the solvent was removed under reduced pressure. The residue was purified by column chromatography using a 40-g SiO2 pre-packed column eluting with EtOAc/heptane, 0:1 to 3:2, v/v over 30 min, yielding 451 mg (54%) of the desired compound. 1H-NMR (400 MHz, CDCl3) δ: 9.90 (s, 1H), 2.81 (s, 2H), 1.72-1.87 (m, 4H), 1.58-1.69 (m, 2H), 1.40-1.53 (m, 4H).

Workup

  1. customwas placed in a 50 mL round-bottom flask
  2. customequipped with a stir bar
  3. customThe solids were removed by filtration
  4. washrinsed with acetone (20 mL)
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was purified by column chromatography
  7. washeluting with EtOAc/heptane, 0:1 to 3:2, v/v over 30 min

Sources & evidence

ORD record
ord-5941587369e64a9eb295a077e11864ac
Source dataset
uspto-grants-2012_07
Patent number
US08232409B2

Reaction notes

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