4-Toluenesulfonyl chloride → (S)-(5-Oxotetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate

HRID 78512Notes

Reaction equation

HRID 78512 reaction equation
[OH:1][CH2:2][C@H:3]1[O:7][C:6](=[O:8])[CH2:5][CH2:4]1.[C:9]1([CH3:19])[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:10]=1>N1C=CC=CC=1>[CH3:19][C:9]1[CH:14]=[CH:13][C:12]([S:15]([O:1][CH2:2][C@@H:3]2[CH2:4][CH2:5][C:6](=[O:8])[O:7]2)(=[O:17])=[O:16])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 2733813(S)-(+)-gamma-Hydroxymethyl-gamma-butyrolactone

Product 1

HCID 2724793(S)-(5-Oxotetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of (S)-5-(hydroxymethyl)dihydrofuran-2(3H)-one, para-toluenesulfonyl chloride and pyridine were processed using the method described in Example 162A to afford the title compound. MS (ESI) m/z 288 (M+18)+.

Sources & evidence

ORD record
ord-54eca40654f64d2e9a09976410959dd5
Source dataset
uspto-grants-2014_09
Patent number
US08841334B2

Reaction notes

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