Methyl Thioglycolate → {[4-Phenyl-1-(4-(2-quinolinylmethoxy)phenyl)butyl]thio}acetic acid, methyl ester

HRID 1029443Notes

Reaction equation

HRID 1029443 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]3[CH:29]=[CH:28][C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[N:21]=3)=[CH:14][CH:13]=2)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:30]([O:34][CH3:35])(=[O:33])[CH2:31][SH:32]>ClCCl>[C:1]1([CH2:7][CH2:8][CH2:9][CH:10]([S:32][CH2:31][C:30]([O:34][CH3:35])=[O:33])[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]3[CH:29]=[CH:28][C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[N:21]=3)=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 16907Methyl ThioglycolateHCID 100685444-Phenyl-1-(4-(2-quinolinylmethoxy)phenyl)butanol

Product 1

HCID 86745621{[4-Phenyl-1-(4-(2-quinolinylmethoxy)phenyl)butyl]thio}acetic acid, methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of the alcohol (1.56 g) (Step II) and methyl thioglycolate (414 μL) in dichloromethane (20 mL) at 0° was added BF3 ·OEt2 (1.10 mL) dropwise. The mixture was stirred at 0° for 1 h and poured onto buffer (pH 7), extracted with dichloromethane and the organic phase was dried and evaporated. Flash chromatography using 20% ethyl acetate/hexane afforded the title compound as a syrup.

Workup

  1. additionpoured onto buffer (pH 7)
  2. extractionextracted with dichloromethane
  3. customthe organic phase was dried
  4. customevaporated

Sources & evidence

ORD record
ord-6f8a012eec53438d8521777a35b83f8e
Source dataset
uspto-grants-1992_04
Patent number
US05102881

Reaction notes

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