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

HRID 1004283

반응식

HRID 1004283 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2721a30731df47dbae90a5f4bb17a228
출처 데이터셋
uspto-grants-2000_04
특허 번호
US06048861

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