Ethyl 4-(3-formylphenoxy)butanoate → Ethyl 4-(3-(2-(7-bromoquinolin-2-yl)ethenyl)phenoxy)butyrate

HRID 1088446Notes

Reaction equation

HRID 1088446 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH3:12])=[N:9]2)=[CH:4][CH:3]=1.[CH:13]([C:15]1[CH:16]=[C:17]([CH:27]=[CH:28][CH:29]=1)[O:18][CH2:19][CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=O>C(OC(=O)C)(=O)C>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH:12]=[CH:13][C:15]3[CH:16]=[C:17]([CH:27]=[CH:28][CH:29]=3)[O:18][CH2:19][CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 10466631Ethyl 4-(3-formylphenoxy)butanoateHCID 123328967-Bromo-2-methylquinoline

Product 1

HCID 53654124Ethyl 4-(3-(2-(7-bromoquinolin-2-yl)ethenyl)phenoxy)butyrate

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A solution of 7-bromoquinaldine (22 g, 0.1M) and ethyl 4-(3-formylphenoxy)butanoate (20 g) in acetic anhydride (100 ml) was heated at 135° for 34 hours cooled and evaporated. Flash chromatography of the residue using 1:1 ether in hexane as eluant afforded crude adduct. Recrystallization from hexane ethyl acetate afforded the title compound: m.p. 92-93°.

Workup

  1. temperaturecooled
  2. customevaporated
  3. customafforded crude adduct
  4. customRecrystallization from hexane ethyl acetate

Sources & evidence

ORD record
ord-c21cad9740eb4d3296b7186bec63de2a
Source dataset
uspto-grants-1990_10
Patent number
US04962203

Reaction notes

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