1,5-Dimethyltetrazole → 1,1-Bis(2-fluoro-4-methylphenyl)-2-(1-methyl-1H-tetrazol-5-yl)ethanol

HRID 2165319Notes

Reaction equation

[CH3:1][N:2]1[C:6]([CH3:7])=[N:5][N:4]=[N:3]1.C([Li])CCC.[F:13][C:14]1[CH:29]=[C:28]([CH3:30])[CH:27]=[CH:26][C:15]=1[C:16]([C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][C:19]=1[F:25])=[O:17]>O1CCCC1>[F:13][C:14]1[CH:29]=[C:28]([CH3:30])[CH:27]=[CH:26][C:15]=1[C:16]([C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][C:19]=1[F:25])([OH:17])[CH2:7][C:6]1[N:2]([CH3:1])[N:3]=[N:4][N:5]=1

Participants

Conditions

Temperature: -10 °C

Procedure

To a solution of 1,5-dimethyltetrazole (4.6 g, 4.7 mmoles) in tetrahydrofuran (40 mL) at -50° C. was added butyl lithium solution (21.4 mL of a 2.2 M solution, 4.7 mmoles). After stirring for 10 minutes, a solution of 2,2'-difluoro-4,4'-dimethylbenzophenone in tetrahydrofuran (15 mL) was added. The solution was stirred for 2.5 hours during which time it was allowed to warm to -10° C. The reaction was quenched by adding 1N hydrochloric acid. The layers were separated and the aqueous layer was extracted with methylene chloride. The combined organic fractions were dried (MgSO4) and evaporated. The residue was triturated with diethyl ether and crystallized from isopropyl acetate to give 8.0 g of the title compound; m.p=150°-151° C. MS: M+ =344.

Workup

stirringThe solution was stirred for 2.5 hours during which time it
customThe reaction was quenched
additionby adding 1N hydrochloric acid
customThe layers were separated
extractionthe aqueous layer was extracted with methylene chloride
dry with materialThe combined organic fractions were dried (MgSO4)
customevaporated
customThe residue was triturated with diethyl ether
customcrystallized from isopropyl acetate

Sources & evidence

ORD record: ord-c55c45413b0d41ac9260d7a68c037e16
Source dataset: uspto-grants-1990_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04939265

Reaction notes

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