Oxygen → E-4-(4-[2-(4-tert-Butylbenzyloxy)phenyl]-2-{2-[4-(1H-tetrazol-5-yl)phenyl]ethyl}but-3-enyl)-2,6-difluorophenol

HRID 1921903Notes

Reaction equation

[C:1]([C:5]1[CH:54]=[CH:53][C:8]([CH2:9][O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2/[CH:17]=[CH:18]/[CH:19]([CH2:33][C:34]2[CH:39]=[C:38]([F:40])[C:37]([O:41][Si](C(C)C)(C(C)C)C(C)C)=[C:36]([F:52])[CH:35]=2)[CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]3[NH:32][N:31]=[N:30][N:29]=3)=[CH:24][CH:23]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O=O.[Cl-].[NH4+]>C1COCC1>[C:1]([C:5]1[CH:54]=[CH:53][C:8]([CH2:9][O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2/[CH:17]=[CH:18]/[CH:19]([CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]3[NH:32][N:31]=[N:30][N:29]=3)=[CH:24][CH:23]=2)[CH2:33][C:34]2[CH:39]=[C:38]([F:40])[C:37]([OH:41])=[C:36]([F:52])[CH:35]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

442 mg (0.51 mmol, 86%-pure) of E-5-{4-[5-[2-(4-tert-butylbenzyloxy)phenyl]-3-(3,5-difluoro-4-triisopropylsilanyloxybenzyl)pent-4-enyl]phenyl}-1H-tetrazole are charged in 12 mol of THF, cooled to 0° C., mixed with 1.18 ml (1.18 mmol) of a 1 M solution of tetra-n-butylammonium fluoride in THF with exclusion of oxygen and stirred at room temperature for 2 hours. The mixture is then added to ammonium chloride solution and extracted with ethyl acetate. The organic phase is dried over sodium sulfate and concentrated. 297 mg (0.5 mmol, 98% of theory) of the title compound are obtained.

Workup

extractionextracted with ethyl acetate
dry with materialThe organic phase is dried over sodium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-817c3f26d02e40539951e75d02b0a477
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08173704B2

Reaction notes

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