2,2,2-Trifluoro-N,N-dimethylacetamide → 7-Phenyl-1-(5-(2,2,2-trifluoroacetyl)oxazol-2-yl)heptan-1-one

HRID 2386183Notes

Reaction equation

HRID 2386183 reaction equation
[Si]([O:8][CH:9]([C:22]1[O:23][C:24]([C:27](=[O:32])[C:28]([F:31])([F:30])[F:29])=[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=CN=1)CCCCCCC1C=CC=CC=1)(C(C)(C)C)(C)C.CN(C)C(=O)C(F)(F)F>>[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](=[O:32])[C:28]([F:31])([F:29])[F:30])=[CH:25][N:26]=2)=[O:8])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 3

HCID 3504912,2,2-Trifluoro-N,N-dimethylacetamideHCID 685237222-(1-{[tert-Butyl(dimethyl)silyl]oxy}-7-phenylheptyl)-1,3-oxazoleHCID 685275541-(2-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)oxazol-5-yl)-2,2,2-trifluoroethanone

Product 1

HCID 119918127-Phenyl-1-(5-(2,2,2-trifluoroacetyl)oxazol-2-yl)heptan-1-oneYield 58%

Procedure

1-(2-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)oxazol-5-yl)-2,2,2-trifluoroethanone. The title compound was prepared from 2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)oxazole (100 mg, 0.268 mmol) and N,N-dimethyltrifluoroacetamide following General Procedure K. Flash chromatography (2-10% EtOAc/hexanes) yielded the title compound as a clear oil (73 mg, 58%): 1H NMR (CDCl3, 600 MHz) δ 8.01 (s, 1H), 7.28-7.26 (m, 2H), 7.18-7.16 (m, 3H), 4.90 (t, 1H, J=7.0 Hz), 2.60 (t, 2H, J=7.5 Hz), 1.96-1.88 (m, 2H), 1.63-1.60 (m, 2H), 1.44-1.35 (m, 6H), 0.90 (s, 9H), 0.09 (s, 3H), 0.01 (s, 3H); 13C NMR (CDCl3, 150 MHz) δ 172.8, 169.2 (q, J=39 Hz), 145.1, 143.5, 140.6, 1292, 129.1, 126.5, 116.6 (q, J=287 Hz), 69.5, 37.1, 36.8, 32.2, 30.0, 29.9, 26.5, 25.7, 19.1, −4.2, −4.3.

Sources & evidence

ORD record
ord-c41764e756d9454b8549246d36742a1d
Source dataset
uspto-grants-2012_09
Patent number
US08268817B2

Reaction notes

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