Dimethylacetamide → 1-(2-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)oxazol-5-yl)ethanone

HRID 2386182Notes

Reaction equation

[Si:1]([O:8][CH:9]([C:22]1[O:23][CH:24]=[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:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CN(C)[C:29](=[O:31])[CH3:30]>>[Si:1]([O:8][CH:9]([C:22]1[O:23][C:24]([C:29](=[O:31])[CH3:30])=[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:4]([CH3:7])([CH3:5])[CH3:6])([CH3:2])[CH3:3]

Participants

Reactant 2

HCID 31374Dimethylacetamide

HCID 685237222-(1-{[tert-Butyl(dimethyl)silyl]oxy}-7-phenylheptyl)-1,3-oxazole

Product 1

HCID 685279471-(2-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)oxazol-5-yl)ethanoneYield 24%

Procedure

The title compound was prepared from 2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)oxazole (50 mg, 0.134 mmol) and N,N-dimethylacetamide following General Procedure K. Flash chromatography (2-10% EtOAc/hexanes) yielded the title compound as a clear oil (14 mg, 24%): 1H NMR (CDCl3, 600 MHz) δ 7.69 (s, 1H), 7.27-7.25 (m, 2H), 7.17-7.15 (m, 3H), 4.83 (t, 1H, J=7.0 Hz), 2.58 (t, 2H, J=7.5 Hz), 2.48 (s, 3H), 1.91-1.84 (m, 2H), 1.61-1.57 (m, 2H), 1.43-1.32 (m, 6H), 0.87 (s, 9H), 0.07 (s, 3H), −0.02 (s, 3H); 13C NMR (CDCl3, 150 MHz) δ 186.7, 169.5, 150.5, 143.6, 134.2, 129.2, 129.1, 126.5, 69.5, 37.2, 36.8, 32.2, 30.0, 30.0, 27.6, 26.5, 25.8, 19.1, −4.2, −4.3.

Sources & evidence

ORD record: ord-29f3f301e0dc41adb93067350956a210
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08268817B2

Reaction notes

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