Ethyl Acetate → HCID 19696747, compound

HRID 863600Notes

Reaction equation

C([C:5]1[N:9]([CH2:10][CH2:11][CH2:12][O:13][C:14]2[C:19]([CH3:20])=[CH:18][C:17]([C:21]3[N:22]=[N:23][N:24]([CH3:26])[N:25]=3)=[CH:16][C:15]=2[CH3:27])[N:8]=[CH:7][N:6]=1)(OC)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+].C(OCC)(=O)C>C1COCC1>[CH3:26][N:24]1[N:23]=[N:22][C:21]([C:17]2[CH:16]=[C:15]([CH3:27])[C:14]([O:13][CH2:12][CH2:11][CH2:10][N:9]3[CH:5]=[N:6][CH:7]=[N:8]3)=[C:19]([CH3:20])[CH:18]=2)=[N:25]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 5-carbomethoxy-1-[3-[4-(2-methyl-tetrazol-5-yl)-2,6-dimethylphenoxy]-propyl]-1,2,4-triazole (868 mg, 2.34 mmol) in 23 ml of THF was added dropwise at 0° C. a solution of 1M LAH in THF (1.52 ml, 1.52 mmol). The mixture was stirred for 20 min at 0° C. and then stirred at 20° C. for 24 h. Rochelle salt solution was added to the mixture and the solution was stirred at 20° C. for 10 min. Ethyl acetate was added to the above mixture and the aqueous layer was extracted with methylene chloride (3×). The combined organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica column chromatography (16 cm column, methylene chloride/acetone, 8/1 - 0/1) to afford 132 mg (18%) of 2-[3-[4-(2-methyl-tetrazol-5-yl)-2,6-dimethylphenoxy]-propyl]-1,2,4-triazole, m.p. 76°-78° C.

Workup

stirringstirred at 20° C. for 24 h
stirringthe solution was stirred at 20° C. for 10 min
extractionthe aqueous layer was extracted with methylene chloride (3×)
dry with materialThe combined organic layer was dried over sodium sulfate
concentrationconcentrated in vacuo
customThe residue was purified by silica column chromatography (16 cm column, methylene chloride/acetone, 8/1 - 0/1)

Sources & evidence

ORD record: ord-259f246ca2194f1c94b1ec29a6690569
Source dataset: uspto-grants-1998_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05721261

Reaction notes

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