Isopropanol → 5-(2,3-dihydro-1-benzofuran-5-yl)-1H-tetrazole

HRID 452602Notes

Reaction equation

[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]#[N:11])=[CH:9][C:4]=2[CH2:3][CH2:2]1.[N-:12]=[N+:13]=[N-:14].[Na+].CC(O)C.[OH-].[Na+]>[Br-].[Zn+2].[Br-].O>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[NH:14][N:13]=[N:12][N:11]=3)=[CH:9][C:4]=2[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 2,3-dihydro-1-benzofuran-5-carbonitrile (1.29 g, 8.89 mmol), sodium azide (1.16 g, 17.78 mmol), zinc bromide (1.00 g, 4.45 mmol), 2-propanol (15 mL) and water (30 mL) was stirred at 80° C. for 48 hr. The reaction mixture was basified with an aqueous sodium hydroxide solution, and washed with ethyl acetate. The aqueous layer was acidified with hydrochloric acid, and extracted with ethyl acetate/tetrahydrofuran. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give the title compound (1.10 g, yield 66%) as colorless crystals.

Workup

washwashed with ethyl acetate
extractionextracted with ethyl acetate/tetrahydrofuran
washThe organic layer was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-b5decc0e3fb24ea48f39f80db87fdd6b
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08492378B2

Reaction notes

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