HCID 14877939, compound → HCID 14877941, compound

HRID 1460324Notes

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 (1.0 M, 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 2 M 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 2 M 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-33808bfd82a24a5f920cbf150f234664
Source dataset: uspto-grants-1991_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05070206

Reaction notes

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