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

HRID 1518151ノート

反応式

HRID 1518151 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-5941587369e64a9eb295a077e11864ac
出典データセット
uspto-grants-2012_07
特許番号
US08232409B2

反応ノート

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