Ether tetrahydrofuran → HCID 49804854, compound

HRID 1627908Notes

Reaction equation

HRID 1627908 reaction equation
[CH2:1]([Mg]Cl)[CH2:2][CH3:3].[CH2:6]([C:8]1[N:13]=[C:12]2[S:14][C:15]3[CH2:20][CH2:19][CH2:18][CH2:17][C:16]=3[C:11]2=[C:10]([C:21]2[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=2)[C:9]=1[CH:28]=[C:29]1[S:33][C:32](=[O:34])[NH:31][C:30]1=[O:35])[CH3:7].C(OCC)C.O1CCCC1>C(OCC)C.[Cu]I>[CH2:6]([C:8]1[N:13]=[C:12]2[S:14][C:15]3[CH2:20][CH2:19][CH2:18][CH2:17][C:16]=3[C:11]2=[C:10]([C:21]2[CH:22]=[CH:23][C:24]([CH3:27])=[CH:25][CH:26]=2)[C:9]=1[CH:28]([CH:29]1[S:33][C:32](=[O:34])[NH:31][C:30]1=[O:35])[CH2:1][CH2:2][CH3:3])[CH3:7]

Participants

6

Reactant 3

HCID 21868444Ether tetrahydrofuranHCID 86662964HCID 86662964, compoundHCID 178455855HCID 178455855, compound

Product 1

HCID 49804854HCID 49804854, compoundYield 9%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3283Diethyl EtherSolvent2×

Procedure

To a cold (−15° C.) solution of copper(I)iodide (0.200 g; 1.05 mmol) in anhydrous diethyl ether (5 mL) was added a 2M solution of n-propylmagnesium chloride in diethyl ether (1.0 mL; 2.0 mmol). The mixture was stirred for 20 min and a solution of 5-[1-(2-ethyl-4-(p-tolyl)-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl)methylene]thiazolidine-2,4-dione (0.083 g; 0.197 mmol) in a mixture diethyl ether-tetrahydrofurane (2/1, 3 mL) was added dropwise and stirring was carried on for 2 h at −15° C. and 18 h at room temperature. The reaction was quenched with a saturated solution of ammonium chloride (50 mL) and diluted with diethyl ether (20 mL). Both phases were separated, the aqueous layer was extracted with diethyl ether, the combined organic phases were washed with a saturated solution of ammonium chloride, dried over magnesium sulphate, filtered and concentrated under reduced pressure. Purification by preparative HPLC (HPLC method 1) furnished 0.008 g (9%) of the title compound.

Workup

  1. stirringstirring
  2. waitwas carried on for 2 h at −15° C. and 18 h at room temperature
  3. customThe reaction was quenched with a saturated solution of ammonium chloride (50 mL)
  4. additiondiluted with diethyl ether (20 mL)
  5. customBoth phases were separated
  6. extractionthe aqueous layer was extracted with diethyl ether
  7. washthe combined organic phases were washed with a saturated solution of ammonium chloride
  8. dry with materialdried over magnesium sulphate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customPurification by preparative HPLC (HPLC method 1)

Sources & evidence

ORD record
ord-e108dbb84a24434ba71a86766182b30a
Source dataset
uspto-grants-2014_07
Patent number
US08785638B2

Reaction notes

Loading…