Tetrahydrofuran → HCID 90005172, compound

HRID 587870Notes

Reaction equation

HRID 587870 reaction equation
C[O:2]/[CH:3]=[CH:4]/[CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:6]1.C1COCC1>CO>[O:2]=[CH:3][CH2:4][CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:6]1

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 118324769HCID 118324769, compound

Product 1

HCID 90005172HCID 90005172, compoundYield 74.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (E)-tert-butyl 3-(2-methoxyvinyl)-3,4-dihydroquinoline-1(2H)-carboxylate (225 mg, 0.778 mmol) in THF (5 mL) dilute HCl (0.2 ml, 6.58 mmol) was added. The reaction mixture was stirred overnight at RT. The progress of reaction was monitored by TLC. After completion of reaction methanol was evaporated under reduced pressure. Further it was purified by flash column chromatography (15% ethyl acetate in hexane) to get the title compound (160 mg, 30.4% yield); m/z-297.6 as Na+1.

Workup

  1. customThe progress of reaction
  2. customwas evaporated under reduced pressure
  3. customFurther it was purified by flash column chromatography (15% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-e91111a3734e437dae4338b5ef5c8600
Source dataset
uspto-grants-2016_01
Patent number
US09227919B2

Reaction notes

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