4-Fluorophenol → Ethanethioic acid trans-(+/-)-S-[5-[(4-fluorophenoxy)methyl]tetrahydro-3-furanyl]ester

HRID 1290361Notes

Reaction equation

HRID 1290361 reaction equation
FC(F)(F)S([O:6][CH2:7][C@@H:8]1[O:12][CH2:11][C@@H:10]([S:13][C:14](=[O:16])[CH3:15])[CH2:9]1)(=O)=O.[F:19][C:20]1[CH:25]=[CH:24][C:23](O)=[CH:22][CH:21]=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[F:19][C:20]1[CH:25]=[CH:24][C:23]([O:6][CH2:7][C@@H:8]2[O:12][CH2:11][C@@H:10]([S:13][C:14](=[O:16])[CH3:15])[CH2:9]2)=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 97324-FluorophenolHCID 81531DiisopropylethylamineHCID 86750748Ethanethioic acid trans(+/-)-S-[tetrahydro-5-[[[(trifluoromethyl)sulfonyl]oxy]methyl]-3-furanyl]ester

Product 1

HCID 86750320Ethanethioic acid trans-(+/-)-S-[5-[(4-fluorophenoxy)methyl]tetrahydro-3-furanyl]esterYield 73.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The title compound is prepared by the procedure of Example 23 using 1.49 g of product from Example 22 in 1 ml of methylene chloride, 0.542 g of 4-fluorophenol, 2.5 ml of Hunig's base and 3 ml of methylene chloride to give 0.963 g of the desired compound.

Sources & evidence

ORD record
ord-cb52d3dd982d4485a34e8cc928132ceb
Source dataset
uspto-grants-1998_05
Patent number
US05750735

Reaction notes

Loading…