Benzophenone → 2(1-Methyltetrazol-5-yl)-1,1-diphenylethanol

HRID 330690Notes

Reaction equation

[CH3:1][N:2]1[C:6]([CH3:7])=[N:5][N:4]=[N:3]1.C([Li])CCC.[C:13]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1COCC1>[CH3:1][N:2]1[C:6]([CH2:7][C:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[OH:20])=[N:5][N:4]=[N:3]1

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of 1,5-dimethyltetrazole (20 g; 0.204 mole) in dry THF (200 mL) was cooled to -78° C. and treated with n-butyllithium (91 mL of 2.5 molar solution in hexane; 0.227 mole) and the mixture stirred at -78° C. for 30 minutes. Benzophenone (31.1 g; 0.171 mole) was added and the mixture stirred at -78° C. for 30 minutes and allowed to warm up to 23° C. and stirred for 15 hours. The mixture was quenched with 2N HCl (100 mL) and extracted with EtOAc (3×150 mL). The combined organic layers were dried (MgSO4) and evaporated. The residue was crystallized from EtOAc-Hexane to afford the title compound as a white solid (10.5 g; 22%); m.p.=175°-176° C. (crystallized from EtOAc-hexane). MS (CI): m/e=281 for (M+H)+ ;

Workup

stirringthe mixture stirred at -78° C. for 30 minutes
temperatureto warm up to 23° C.
stirringstirred for 15 hours
customThe mixture was quenched with 2N HCl (100 mL)
extractionextracted with EtOAc (3×150 mL)
dry with materialThe combined organic layers were dried (MgSO4)
customevaporated
customThe residue was crystallized from EtOAc-Hexane

Sources & evidence

ORD record: ord-3884a5a71c084908aa2492a1684d494f
Source dataset: uspto-grants-1990_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04897490

Reaction notes

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