Sodium methanolate methanol → trans-(+/-)-5-[[(4-Fluorophenyl)sulfonyl]methyl]tetrahydro-3-furanthiol

HRID 1290359Notes

Reaction equation

HRID 1290359 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][C@@H:12]2[O:16][CH2:15][C@@H:14]([S:17]C(=O)C)[CH2:13]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C[O-].[Na+].CO>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][C@@H:12]2[O:16][CH2:15][C@@H:14]([SH:17])[CH2:13]2)(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 23694274Sodium methanolate methanolHCID 86750317Ethanethioic acid trans-(+/-)-S-[5-[[(4-fluorophenyl)sulfonyl]methyl]tetrahydro-3-furanyl]ester

Product 1

HCID 86750319trans-(+/-)-5-[[(4-Fluorophenyl)sulfonyl]methyl]tetrahydro-3-furanthiolYield 63.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound is prepared by the procedure of Example 16 using 0.955 g of product from Example 31, 0.72 ml of 25% sodium methoxide/methyl alcohol and 10 ml of tetrahydrofuran to give 0.523 g of the desired product.

Sources & evidence

ORD record
ord-a82287475ad2471eb092b5d8bcd87abe
Source dataset
uspto-grants-1998_05
Patent number
US05750735

Reaction notes

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