Diethyl Ether → Dimethyl 5-(3-((7-chloroquinolin-2-yl-methyl)oxy)phenyl)-4,6-dithianonanedioate

HRID 22585Notes

Reaction equation

HRID 22585 reaction equation
Br[CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][C:7]([Cl:13])=[CH:8][CH:9]=2)[N:4]=1.[OH:14][C:15]1[CH:16]=[C:17]([CH:21]([S:29][CH2:30][CH2:31][C:32]([O:34][CH3:35])=[O:33])[S:22][CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])[CH:18]=[CH:19][CH:20]=1.C([O-])([O-])=O.[K+].[K+].CCOCC>C(C(C)=O)C>[Cl:13][C:7]1[CH:6]=[C:5]2[C:10]([CH:11]=[CH:12][C:3]([CH2:2][O:14][C:15]3[CH:16]=[C:17]([CH:21]([S:22][CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])[S:29][CH2:30][CH2:31][C:32]([O:34][CH3:35])=[O:33])[CH:18]=[CH:19][CH:20]=3)=[N:4]2)=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 9997621Dimethyl 5-(3-hydroxyphenyl)-4,6-dithianonanedioateHCID 102441602-(Bromomethyl)-7-chloroquinoline

Product 1

HCID 9984156Dimethyl 5-(3-((7-chloroquinolin-2-yl-methyl)oxy)phenyl)-4,6-dithianonanedioate

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 2-bromomethyl-7-chloroquinoline (2.5 g) (Step 2), phenol (Step 1) (3.4 g) and K2CO3 (3 g) was heated at reflux for 4 hours in methyl ethyl ketone (100 ml). The reaction mixture was cooled and ether (100 ml) was added. The suspension was filtered and evaporated. Flash chromatography of the residue using 30% ethyl acetate in hexane afforded the title compound.

Workup

  1. temperaturewas heated
  2. temperatureThe reaction mixture was cooled
  3. filtrationThe suspension was filtered
  4. customevaporated

Sources & evidence

ORD record
ord-86bc6ded7c5243dc8a634f420e63159d
Source dataset
uspto-grants-1995_06
Patent number
US05428171

Reaction notes

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