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

HRID 1518151노트

반응식

HRID 1518151 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-5941587369e64a9eb295a077e11864ac
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08232409B2

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