Dibutyltin oxide → 5-(3-Benzyloxy-benzyl)-1,2,3,4-tetrazole

HRID 902608

Reaction equation

[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:15][C:16]#[N:17])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([N:22]=[N+:23]=[N-:24])(C)C.C([Sn](=O)CCCC)CCC>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:12]=[CH:13][CH:14]=1)[CH2:15][C:16]1[NH:24][N:23]=[N:22][N:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To a stirring solution of 3-benzyloxyphenylacetonitrile (2.0 g, 8.95 mmol) in toluene (17 ml) was added trimethylsilylazide (2.37 g, 17.9 mmol) and di-n-butyltin oxide (0.22 g, 0.9 mmol). The mixture was heated at 110° C. for 48 h, and was concentrated. The reaction mixture was dissolved in ethyl acetate (100 ml) and washed two times with 10% aqueous sodium bicarbonate. The basic extracts were acidified to pH<2 with conc. HCl, and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered, and concentrated. The crude product (2.0 g, 89%) was used in the next step without further purification. MS (ESI) 267.0 (M+H+).

Workup

concentrationwas concentrated
dissolutionThe reaction mixture was dissolved in ethyl acetate (100 ml)
washwashed two times with 10% aqueous sodium bicarbonate
extractionthe aqueous layer was extracted with ethyl acetate
dry with materialThe combined organic layers were dried over sodium sulfate
filtrationfiltered
concentrationconcentrated
customThe crude product (2.0 g, 89%) was used in the next step without further purification

Sources & evidence

ORD record: ord-7cab76fffd884cd9a77fdd4960ec9208
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07365085B2

Linked notes

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