Tributylstannane → 5-Methyl-2-[3-[4-(2-methyl-tetrazol-5-yl)-2,6-dimethylphenoxy]-propyl]-1,2,4-triazole

HRID 863599Notes

Reaction equation

O(C(O[CH2:11][C:12]1[N:13]=[CH:14][N:15]([CH2:17][CH2:18][CH2:19][O:20][C:21]2[C:26]([CH3:27])=[CH:25][C:24]([C:28]3[N:29]=[N:30][N:31]([CH3:33])[N:32]=3)=[CH:23][C:22]=2[CH3:34])[N:16]=1)=S)C1C=CC=CC=1.CC(N=NC(C#N)(C)C)(C#N)C.C([SnH](CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[CH3:11][C:12]1[N:13]=[CH:14][N:15]([CH2:17][CH2:18][CH2:19][O:20][C:21]2[C:22]([CH3:34])=[CH:23][C:24]([C:28]3[N:29]=[N:30][N:31]([CH3:33])[N:32]=3)=[CH:25][C:26]=2[CH3:27])[N:16]=1

Participants

Conditions

Temperature: 75 °C

Procedure

To a solution of 5-phenoxythiocarbonyloxymethyl-2-[3-[4-(2-methyl-tetrazol-5-yl)-2,6-dimethylphenoxy]-propyl]-1,2,4-triazole (130 mg, 0.79 mmol) in 20 ml of toluene was added AIBN (130 mg, 0.79 mmol) and tributyltin hydride (3.2 g, 11 mmol) and the mixture was stirred at 75° C. for 6.5 h. The solvent was concentrated in vacuo and the residue was purified by silica column chromatography (10 cm column, ethyl acetate/hexane, 1/1 - 5/1; methylene chloride/acetone, 4/1 - 0/1) to afford 142 mg (43%) of 5-methyl-2-[3-[4-(2-methyl-tetrazol-5-yl)-2,6-dimethylphenoxy]-propyl]-1,2,4-triazole, m.p. 101°-103° C.

Workup

concentrationThe solvent was concentrated in vacuo
customthe residue was purified by silica column chromatography (10 cm column, ethyl acetate/hexane, 1/1 - 5/1; methylene chloride/acetone, 4/1 - 0/1)

Sources & evidence

ORD record: ord-5abf88466d9d4528aa548655bbd78b3d
Source dataset: uspto-grants-1998_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05721261

Reaction notes

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