Ethyl Acetate → 3-(2-(7-Chloroquinolin-2-yl)cyclopropyl)benzaldehyde

HRID 22598Notes

Reaction equation

HRID 22598 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH:12]3[CH2:14][CH:13]3[C:15]3[CH:16]=[C:17]([CH:21]4OCC[O:22]4)[CH:18]=[CH:19][CH:20]=3)=[N:9]2)=[CH:4][CH:3]=1.CCOC(C)=O>C1COCC1.CC(O)=O.O>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH:12]3[CH2:14][CH:13]3[C:15]3[CH:16]=[C:17]([CH:18]=[CH:19][CH:20]=3)[CH:21]=[O:22])=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 104057212-(3-(2-(7-Chloroquinolin-2-yl)cyclopropyl)phenyl)1,3-dioxolane

Product 1

HCID 104479623-(2-(7-Chloroquinolin-2-yl)cyclopropyl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 21877175AcOH THF waterSolvent

Procedure

The dioxolane (step 3) (500 mg, 1.42 mmoles) was heated at reflux in 9 mL of THF:AcOH:H2O 6:2:1 for 2 hours. Addition of 25% NH4OAc, extraction with EtOAc, drying, evaporation, and flash chromatography on silica with EtOAc:toluene 2.5:97.5 afforded the title compound.

Workup

  1. customdrying
  2. customevaporation, and flash chromatography on silica with EtOAc:toluene 2.5:97.5

Sources & evidence

ORD record
ord-587e58b6fba14d42ba8d726ca562288a
Source dataset
uspto-grants-1995_06
Patent number
US05428171

Reaction notes

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