18-Crown-6 → 2-Benzenesulfonylmethyl-benzooxazole

HRID 602787Notes

Reaction equation

HRID 602787 reaction equation
Br[CH2:2][C:3]1[O:4][C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[Na+].[C:13]1([S:19]([O-:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C1OCCOCCOCCOCCOCCOC1>CC#N>[C:13]1([S:19]([CH2:2][C:3]2[O:4][C:5]3[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=3[N:7]=2)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 2855718-Crown-6HCID 2723840Benzenesulfinic acid, sodium saltHCID 127459442-(Bromomethyl)benzo[d]oxazole

Product 1

HCID 124753982-Benzenesulfonylmethyl-benzooxazoleYield 70%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 9.1 g (0.043 mol) of 2-bromomethyl-benzooxazole in CH3CN (300 mL) were added 7.39 g (0.045 mol, 1.05 eq) of benzenesulfinic acid sodium salt and 2.27 g (8.6 mmol, 0.2 eq) of 18-crown-6. Stirring was continued overnight, solvent evaporated and a column chromatography afforded 8.1 g (70%) of 2-benzenesulfonylmethyl-benzooxazole as a white solid, MS: 274 (H+). (Y. Nagao, S. Yamada, E. Fujita, Tet. Lett., 1983, 24, 2291)

Workup

  1. customsolvent evaporated

Sources & evidence

ORD record
ord-c29c9a0c22224811a7955def82770b32
Source dataset
uspto-grants-2011_03
Patent number
US07906546B2

Reaction notes

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