HCID 14877939, compound → HCID 14877941, compound

HRID 1608395Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)=[C:9]([N:15]2[C:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[N:18][N:17]=[N:16]2)[C:10](OCC)=[O:11])=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:26]2[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=2)=[C:9]([N:15]2[C:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[N:18][N:17]=[N:16]2)[CH2:10][OH:11])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: -80 °C

Procedure

To a solution of 3.5 g (8.2 mmoles) of ethyl 3,3-bis-(4-fluorophenyl)-2-(5-phenyl-1H-tetrazol-1-yl)-2-propenoate in 75 mL of dry methylene chloride at -80° C. under argon was added dropwise 18 mL (1.0M, 18 mmoles) of diisobutylaluminum hydride in methylene chloride. The clear solution was stirred at -80° C. for 10 minutes then monitored by TLC. An additional 5 mL of diisobutylaluminum hydride in methylene chloride was added to the mixture and stirring was continued for 30 minutes. The reaction mixture was quenched with 2M HCl and the product was extracted into ethyl acetate. The organic layers were combined, dried over MgSO4 and evaporated to a semi-solid. Recrystallization from ethyl acetate-hexanes mixture gave 3.2 g (99%) of the title compound; m.p.=196.6°-197.6° C.

Workup

stirringstirring
waitwas continued for 30 minutes
customThe reaction mixture was quenched with 2M HCl
extractionthe product was extracted into ethyl acetate
dry with materialdried over MgSO4
customevaporated to a semi-solid
customRecrystallization from ethyl acetate-hexanes mixture

Sources & evidence

ORD record: ord-173561364b194d26b312a4cf75ce2b44
Source dataset: uspto-grants-1989_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04870187

Reaction notes

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