Potassium Carbonate → HCID 15752886, compound

HRID 1087591Notes

Reaction equation

HRID 1087591 reaction equation
[O:1]=[C:2]([C:6]1[S:7][CH:8]=[CH:9][CH:10]=1)[C:3]([OH:5])=[O:4].S(Cl)(Cl)=O.[CH2:15]([N:17]([CH2:24][CH3:25])[CH2:18][C:19]#[C:20][CH:21](O)[CH3:22])[CH3:16].C(=O)([O-])[O-].[K+].[K+]>ClCCl.O.N1C=CC=CC=1>[O:1]=[C:2]([C:6]1[S:7][CH:8]=[CH:9][CH:10]=1)[C:3]([O:5][CH:21]([CH3:22])[C:20]#[C:19][CH2:18][N:17]([CH2:24][CH3:25])[CH2:15][CH3:16])=[O:4]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 24386Thionyl ChlorideHCID 776942-Thiopheneglyoxylic acidHCID 1144135-(Diethylamino)pent-3-yn-2-ol

Product 1

HCID 15752886HCID 15752886, compoundYield 30.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4.3 g α-oxo-2-thiopheneacetic acid in dichloromethane was added 0.5 ml pyridine, and 6.75 g thionyl chloride was then added dropwise under ice cooling. The mixture was heated under reflux for seven hours and concentrated under reduced pressure, diethyl ether was added to the residue, the insoluble matters were filtered off, and the filtrate was concentrated under reduced pressure. The oily substance thus obtained (4.1 g) was added dropwise to an etheral solution of 4.5 g 5-diethylamino-3-pentyn-2-ol under ice cooling, and the mixture was stirred for 18 hours under cooling with water and basified with an aqueous solution of potassium carbonate. The separated etheral layer was collected, washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The oily residue was purified by silica gel column chromatography (Wako Gel C-200; ethyl acetate), giving 2.48 g of the objective compound as oil.

Workup

  1. additionwas then added dropwise under ice cooling
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for seven hours
  4. concentrationconcentrated under reduced pressure, diethyl ether
  5. additionwas added to the residue
  6. filtrationthe insoluble matters were filtered off
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe oily substance thus obtained (4.1 g)
  9. customThe separated etheral layer was collected
  10. washwashed with water
  11. dry with materialdried over anhydrous magnesium sulfate
  12. concentrationconcentrated under reduced pressure
  13. customThe oily residue was purified by silica gel column chromatography (Wako Gel C-200; ethyl acetate)

Sources & evidence

ORD record
ord-721ca0e7c8454ee68022001a1b6aecdc
Source dataset
uspto-grants-1991_07
Patent number
US05036098

Reaction notes

Loading…