(S)-(+)-Glycidyl-4-nitrobenzoate → (S)-5-(4-glycidyloxybenzo(b)furan-2-yl)-2-methyl-1,3,4-oxadiazole

HRID 2085147Notes

Reaction equation

HRID 2085147 reaction equation
[OH:1][C:2]1[C:10]2[CH:9]=[C:8]([C:11]3[O:12][C:13]([CH3:16])=[N:14][N:15]=3)[O:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.S(C1C=CC([N+]([O-])=O)=CC=1)(O[CH2:21][C@H:22]1[O:24][CH2:23]1)(=O)=O>>[CH2:21]([O:1][C:2]1[C:10]2[CH:9]=[C:8]([C:11]3[O:12][C:13]([CH3:16])=[N:14][N:15]=3)[O:7][C:6]=2[CH:5]=[CH:4][CH:3]=1)[C@H:22]1[O:24][CH2:23]1

Participants

3

Reactant 2

HCID 10868995(S)-(+)-Glycidyl-4-nitrobenzoateHCID 1357943242-(5-Methyl-1,3,4-oxadiazol-2-yl)benzofuran-4-ol

Product 1

HCID 60078060(S)-5-(4-glycidyloxybenzo(b)furan-2-yl)-2-methyl-1,3,4-oxadiazoleYield 28.3%

Procedure

By the reactions in the same manner as in Starting Material Synthesis Example 1 using 2-(4-hydroxybenzo(b)furan-2-yl)-5-methyl-1,3,4-oxadiazole (3.3 g) and (S)-glycidyl nosylate (3.7 g), the title compound (1.1 g) was obtained as white crystals.

Sources & evidence

ORD record
ord-8b6c69defb74450f8a01eccd0877b49f
Source dataset
uspto-grants-2004_04
Patent number
US06720320B2

Reaction notes

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