2-(1-{[tert-Butyl(dimethyl)silyl]oxy}-7-phenylheptyl)-1,3-oxazole → 2-(7-Phenylheptanoyl)oxazole-5-carbaldehyde

HRID 2386184Notes

Reaction equation

HRID 2386184 reaction equation
[Si]([O:8][CH:9]([C:22]1[O:23][C:24]([CH:27]=[O:28])=[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:16]1([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C:9]([C:22]2[O:23][C:24]([CH:27]=[O:28])=[CH:25][N:26]=2)=[O:8])[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 685237222-(1-{[tert-Butyl(dimethyl)silyl]oxy}-7-phenylheptyl)-1,3-oxazoleHCID 866401522-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)oxazole-5-carbaldehyde

Product 1

HCID 119918942-(7-Phenylheptanoyl)oxazole-5-carbaldehydeYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)oxazole-5-carbaldehyde. The title compound was prepared from 2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)oxazole (122 mg, 0.327 mmol) and N,N-dimethylformamide following General Procedure K. Flash chromatography (2-10% EtOAc/hexanes) yielded the title compound as a clear oil (114 mg, 87%): 1H NMR (CDCl3, 600 MHz) δ 9.77 (s, 1H), 7.78 (s, 1H), 7.27-7.25 (m, 2H), 7.17-7.15 (m, 3H), 4.86 (t, 1H, J=7.0 Hz), 2.58 (t, 2H, J=7.5 Hz), 1.91-1.85 (m, 2H), 1.62-1.57 (m, 2H), 1.43-1.33 (m, 6H), 0.88 (s, 9H), 0.07 (s, 3H), −0.02 (s, 3H); 13C NMR (CDCl3, 150 MHz) δ 177.5, 170.8, 150.5, 143.6, 137.8, 129.2, 129.1, 126.5, 69.5, 37.2, 36.8, 32.2, 29.9, 29.9, 26.5, 25.8, 19.1, −4.2, −4.3.

Sources & evidence

ORD record
ord-f9aba6a868e54a91a3ec899eefd1b04c
Source dataset
uspto-grants-2012_09
Patent number
US08268817B2

Reaction notes

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