Dimethyl (2-oxopropyl)phosphonate → 4-(Quinolin-3-yl)-but-3-en-2-one

HRID 1837920

反応式

HRID 1837920 の反応式
[O:1]=[C:2]([CH3:10])[CH2:3]P(=O)(OC)OC.[Li+].[Cl-].[N:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[C:15]([CH:23]=O)[CH:14]=1.C1CCN2C(=NCCC2)CC1>C(#N)C>[N:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[C:15]([CH:23]=[CH:3][C:2](=[O:1])[CH3:10])[CH:14]=1

参加物

6

反応物 4

HCID 77872Dimethyl (2-oxopropyl)phosphonateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 836413-QuinolinecarboxaldehydeHCID 433294Lithium Chloride

生成物 1

HCID 541844574-(Quinolin-3-yl)-but-3-en-2-one

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

Dimethyl (2-oxopropyl)phosphonate (3.1 g,19.1 mmol), anhydrous LiCl (972 mg, 23 mmol), and 3-quinoline carboxaldehyde 6-1 (3.0 g,19.1 mmol) in anhydrous acetonitrile (70 mL), was treated with DBU (2.9 mL, 19.1 mmol) and the resulting suspension stirred at room temperature for 1 h. The solvent was removed at reduced pressure and the resulting residue partitioned between brine and methylene chloride. The organic layer was removed, dried, and concentrated to afford a yellow solid which was recrystallized from ethyl acetate/hexanes to afford 22-1 as an off-white solid.

後処理

  1. customThe solvent was removed at reduced pressure
  2. customthe resulting residue partitioned between brine and methylene chloride
  3. customThe organic layer was removed
  4. customdried
  5. concentrationconcentrated
  6. customto afford a yellow solid which
  7. customwas recrystallized from ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-73a8388a28324993b36ddb2ac2278bcc
出典データセット
uspto-grants-2004_08
特許番号
US06784190B2

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