Tetrahydrofuran → 5-(2,4-Difluorophenyl)tetrahydro-3-furanthiol

HRID 54797Notes

Reaction equation

HRID 54797 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[O:13][CH2:12][CH:11]([S:14]C(=O)C)[CH2:10]1.C[O-].[Na+].CO.O1CCCC1.Cl.C(O)(C)C>C(OCC)(=O)C.CCCCCC>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[O:13][CH2:12][CH:11]([SH:14])[CH2:10]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 21912024Isopropanol hydrochlorideHCID 23694274Sodium methanolate methanolHCID 85719043(+/-)-Ethanethioic acid S-[5-(2,4-difluorophenyl)tetrahydro-3-furanyl]ester

Product 1

HCID 189239905-(2,4-Difluorophenyl)tetrahydro-3-furanthiolYield 86%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

The title compound is prepared by the procedure of Example 16 using 0.250 g of product from Example 166, 243 μl of 25% sodium methoxide/methyl alcohol, 4.5 ml of tetrahydrofuran and 530 μl of 2N hydrochloric acid/isopropyl alcohol to give, after chromatography (silica gel: 5-10% ethyl acetate/hexane), 0.180 g of the desired product, as mixture of isomers.

Workup

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Sources & evidence

ORD record
ord-f1864d29e7ed46e3befaec6c6329fa68
Source dataset
uspto-grants-1997_04
Patent number
US05623081

Reaction notes

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