4-Fluoroiodobenzene → 1-(5-(4-Fluorophenyl)oxazol-2-yl)-7-phenylheptan-1-one

HRID 605616Notes

Reaction equation

HRID 605616 reaction equation
[Si]([O:8][CH:9]([C:22]1[O:23][C:24]([C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)=[CH:25][N:26]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(C(C)(C)C)(C)C.[Si](OC(C1OC([Sn](CCCC)(CCCC)CCCC)=CN=1)CCCCCCC1C=CC=CC=1)(C(C)(C)C)(C)C.FC1C=CC(I)=CC=1>>[F:33][C:30]1[CH:29]=[CH:28][C:27]([C:24]2[O:23][C:22]([C:9](=[O:8])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[N:26][CH:25]=2)=[CH:32][CH:31]=1

Participants

4

Reactant 3

HCID 96054-FluoroiodobenzeneHCID 161106132-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)-5-(4-fluorophenyl)oxazoleHCID 670460482-(1-(Tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole

Product 1

HCID 161106451-(5-(4-Fluorophenyl)oxazol-2-yl)-7-phenylheptan-1-oneYield 61%

Procedure

2-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)-5-(4-fluorophenyl)oxazole. The title compound was prepared from 2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole (81 mg, 0.122 mmol) and 1-fluoro-4-iodobenzene following General Procedure A. Flash chromatography (2% EtOAc/hexanes) yielded the title compound as a clear oil (40 mg, 61%): 1H NMR (CDCl3, 600 MHz) δ 7.63-7.61 (m, 2H), 7.27-7.24 (m, 4H), 7.17-7.11 (m, 4H), 4.88 (t, 1H, J=6.0 Hz), 2.58 (t, 2H, J=7.5 Hz), 1.95-1.90 (m, 2H), 1.62-1.59 (m, 2H), 1.46-1.35 (m, 6H), 0.89 (s, 9H), 0.10 (s, 3H), −0.01 (s, 3H); 13C NMR (CDCl3, 150 MHz) δ 165.9, 163.5 (d, J=258 Hz), 151.5, 143.6, 129.2, 129.1, 127.1 (d, J=8.3 Hz), 126.4, 124.8, 121.1, 117.0 (d, J=22 Hz), 69.4, 37.3, 36.8, 32.3, 30.0, 26.6, 26.6, 25.9, 19.1, −4.1, −4.2.

Sources & evidence

ORD record
ord-bb5a1b4bec59470cbe63994f3bcef45a
Source dataset
uspto-grants-2011_03
Patent number
US07915270B2

Reaction notes

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