Boron trifluoride etherate → Methyl ((1-(((4-chlorophenyl)methyl)thio)-1-(4-(2-quinolinylmethoxy)phenyl)methyl)thio)acetate

HRID 1029461Notes

Reaction equation

HRID 1029461 reaction equation
B(F)(F)F.CCOCC.[N:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][C:11]=1[CH2:20][O:21][C:22]1[CH:29]=[CH:28][C:25]([CH:26]=O)=[CH:24][CH:23]=1.[C:30]([O:34][CH3:35])(=[O:33])[CH2:31][SH:32].[Cl:36][C:37]1[CH:44]=[CH:43][C:40]([CH2:41][SH:42])=[CH:39][CH:38]=1>C(Cl)Cl>[Cl:36][C:37]1[CH:44]=[CH:43][C:40]([CH2:41][S:42][CH:26]([S:32][CH2:31][C:30]([O:34][CH3:35])=[O:33])[C:25]2[CH:28]=[CH:29][C:22]([O:21][CH2:20][C:11]3[CH:12]=[CH:13][C:14]4[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=4)[N:10]=3)=[CH:23][CH:24]=2)=[CH:39][CH:38]=1

Participants

6

Reactant 4

HCID 8000Boron trifluoride etherateHCID 16907Methyl ThioglycolateHCID 804094-Chlorobenzyl mercaptanHCID 145789604-(2-quinolinylmethoxy)Benzaldehyde

Product 1

HCID 54306383Methyl ((1-(((4-chlorophenyl)methyl)thio)-1-(4-(2-quinolinylmethoxy)phenyl)methyl)thio)acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

At 0° C., BF3 /Et2O (380 μL, 2.3 equiv.) was added to a solution of 4-(2-quinolinylmethoxy)benzaldehyde (Example 1, Step 1, 352 mg, 1.34 mmoles), methyl thioglycolate (130 μL, 1.1 equiv.) and 4-chlorobenzyl mercaptan (195 μL, 1.1 equiv.) in CH2Cl2 (7 mL) and the mixture was stirred at 0° C. an hour and at room temperature 15 minutes. 25% Aqueous NH4OAc was then added at 0° C. and the products were extracted with EtOAc, dried over Na2SO4 and separated by flash chromatography on silica using EtOAc:toluene 2.5:97.5 and 5:95 to yield the title compound.

Workup

  1. extractionthe products were extracted with EtOAc
  2. dry with materialdried over Na2SO4
  3. customseparated by flash chromatography on silica

Sources & evidence

ORD record
ord-9e3b1ae7584c42c4b1374c239e1ab5e3
Source dataset
uspto-grants-1992_04
Patent number
US05102881

Reaction notes

Loading…