2-(2-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)oxazol-5-yl)phenol → 1-(5-(2-Hydroxyphenyl)oxazol-2-yl)-7-phenylheptan-1-one

HRID 605634Notes

Reaction equation

HRID 605634 reaction equation
[Si]([O:8][CH:9]([C:22]1[O:23][C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[OH:33])=[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>CCOC(C)=O>[OH:33][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[C:24]1[O:23][C:22]([C:9](=[O:8])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[N:26][CH:25]=1

Participants

3

Reactant 1

HCID 161106022-(2-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)oxazol-5-yl)phenol

Product 1

HCID 161106341-(5-(2-Hydroxyphenyl)oxazol-2-yl)-7-phenylheptan-1-oneYield 12%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The title compound was prepared from 2-(2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)oxazol-5-yl)phenol (44 mg, 0.094 mmol) following General Procedure D. Preparative thin layer chromatography (30% EtOAc) yielded the title compound as a white solid (3.4 mg, 12%): 1H NMR (CDCl3, 500 MHz) δ 7.94-7.93 (m, 1H), 7.82 (br s, 1H), 7.38-7.34 (m, 4H), 7.26-7.25 (m, 3H), 7.12 (t, 1H, J=15.0 Hz), 7.00 (d, 1H, J=8.0 Hz), 3.18 (t, 2H, J=7.5 Hz), 2.69 (t, 2H, J=7.5 Hz), 1.89-1.83 (m, 2H), 1.75-1.69 (m, 2H), 1.54-1.46 (m, 4H); 13C NMR (CDCl3, 125 MHz) δ 188.8, 153.4, 151.7, 143.1, 131.3, 128.8, 128.7, 127.7, 127.5, 126.0, 121.7, 116.9, 114.5, 39.4, 36.3, 31.7, 29.5, 29.4, 24.5; MALDI-FTMS m/z 350.1751 (M+H+, C22H24NO3, requires 350.1751).

Sources & evidence

ORD record
ord-c39ddb6348ca4d829d456820308c7624
Source dataset
uspto-grants-2011_03
Patent number
US07915270B2

Reaction notes

Loading…