4'-Bromo-2,2,2-trifluoroacetophenone → 7-Phenyl-1-(5-(4-(2,2,2-trifluoroacetyl)phenyl)oxazol-2-yl)heptan-1-one

HRID 605610Notes

Reaction equation

HRID 605610 reaction equation
[Si]([O:8][CH:9]([C:22]1[O:23][C:24]([C:27]2[CH:32]=[CH:31][C:30]([C:33](=[O:38])[C:34]([F:37])([F:36])[F:35])=[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.BrC1C=CC(C(=O)C(F)(F)F)=CC=1>>[C:16]1([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C:9]([C:22]2[O:23][C:24]([C:27]3[CH:32]=[CH:31][C:30]([C:33](=[O:38])[C:34]([F:37])([F:35])[F:36])=[CH:29][CH:28]=3)=[CH:25][N:26]=2)=[O:8])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 3

HCID 6038664'-Bromo-2,2,2-trifluoroacetophenoneHCID 161106161-(4-(2-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)oxazol-5-yl)phenyl)-2,2,2-trifluoroethanoneHCID 670460482-(1-(Tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole

Product 1

HCID 161106487-Phenyl-1-(5-(4-(2,2,2-trifluoroacetyl)phenyl)oxazol-2-yl)heptan-1-oneYield 69%

Procedure

1-(4-(2-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)oxazol-5-yl)phenyl)-2,2,2-trifluoroethanone. The title compound was prepared from 2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole (55 mg, 0.083 mmol) and 1-(4-bromophenyl)-2,2,2-trifluoroethanone following General Procedure A. Flash chromatography (5-20% EtOAc/hexanes) yielded the title compound as a white solid (31 mg, 69%): 1H NMR (CDCl3, 600 MHz) δ 8.13-8.12 (d, 2H, J=7.8 Hz), 7.80-7.79 (d, 2H, J=7.8 Hz), 7.49 (s, 1H), 7.27-7.24 (m, 2H), 7.16-7.15 (m, 3H), 4.86 (t, 1H, J=6.0 Hz), 2.59 (t, 2H, J=7.5 Hz), 1.95-1.91 (m, 2H), 1.61-1.59 (m, 2H), 1.37-1.34 (m, 6H), 0.90 (s, 9H), 0.10 (s, 3H), 0.00 (s, 3H); 13C NMR (CDCl3, 150 MHz) δ 180.4 (d, J=35 Hz), 167.5, 150.3, 143.6, 135.1, 131.8, 129.9, 129.2, 129.1, 126.5, 126.1, 125.1, 117.6 (d, J=290 Hz), 69.6, 37.3, 36.8, 32.3, 30.0, 36.6, 26.6, 26.0, 19.1, −4.1, −4.2.

Sources & evidence

ORD record
ord-fc7154c75fec45be8bc677e9e0119334
Source dataset
uspto-grants-2011_03
Patent number
US07915270B2

Reaction notes

Loading…