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

HRID 379263

Reaction equation

HRID 379263 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-5b049ef5f06d40b68074090640c886ab
Source dataset
uspto-grants-2001_10
Patent number
US06297249B1

Linked notes

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