Tetrahydrofuran → HCID 18922202, compound

HRID 1289756Notes

Reaction equation

HRID 1289756 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:11])[C:5](=[CH:9][CH:10]=1)[C:6]([OH:8])=[O:7].[H-].[Na+].[CH2:14](I)[CH2:15][CH3:16].O1C[CH2:21][CH2:20][CH2:19]1>CN(C)C=O>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH2:14][CH2:15][CH3:16])=[O:7])=[C:4]([O:11][CH2:19][CH2:20][CH3:21])[CH:3]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 787824-Chlorosalicylic acid

Product 1

HCID 18922202HCID 18922202, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The synthesis was carried out according to the method of Example 18-(1). 4-Chlorosalicylic acid (8.5 g), : 60% oil sodium hydride (4.5 g), n-propyl iodide (50 g), tetrahydrofuran (30 ml) and dimethylformamide (25 ml) were used as reagents. The mixture was reacted for 1 hour at 90° C. After the reaction, the mixture was chromatographed on silica gel (hexane-ethyl acetate) to give 7.63 g of a colorless transparent liquid (yield 63%).

Workup

  1. customThe mixture was reacted for 1 hour at 90° C
  2. customAfter the reaction
  3. customthe mixture was chromatographed on silica gel (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-e8e7778dc779443699d8c2f4bf164456
Source dataset
uspto-grants-1998_05
Patent number
US05750545

Reaction notes

Loading…