2-Iodophenol → 1-(5-(2-Hydroxyphenyl)oxazol-2-yl)-7-phenylheptan-1-one

HRID 605633Notes

Reaction equation

HRID 605633 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.[Si](OC(C1OC([Sn](CCCC)(CCCC)CCCC)=CN=1)CCCCCCC1C=CC=CC=1)(C(C)(C)C)(C)C.IC1C=CC=CC=1O>>[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

4

Reactant 3

HCID 107842-IodophenolHCID 161106022-(2-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)oxazol-5-yl)phenolHCID 670460482-(1-(Tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole

Product 1

HCID 161106341-(5-(2-Hydroxyphenyl)oxazol-2-yl)-7-phenylheptan-1-oneYield 34%

Procedure

2-(2-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)oxazol-5-yl)phenol. The title compound was prepared from 2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole (88 mg, 0.134 mmol) and 2-iodophenol following General Procedure A. Flash chromatography (10-30% EtOAc/hexanes) yielded the title compound as a clear oil (21 mg, 34%): 1H NMR (CDCl3, 500 MHz) δ 7.80-7.76 (m, 1H), 7.62 (s, 1H), 7.56 (br s, 1H), 7.36-7.20 (m, 6H), 7.09-7.04 (m, 2H), 4.94 (t, 1H, J=6.0 Hz), 2.62 (t, 2H, J=7.5 Hz), 2.05-1.93 (m, 2H), 1.68-1.65 (m, 2H), 1.47-1.32 (m, 6H), 0.97 (s, 9H), 0.17 (s, 3H), 0.07 (s, 3H); 13C NMR (CDCl3, 125 MHz) δ 166.3, 154.3, 148.8, 143.2, 130.0, 128.8, 128.6, 126.5, 126.0, 124.9, 119.2, 116.8, 115.6, 70.1, 37.0, 35.3, 31.8, 29.6, 26.2, 26.2, 25.5, 18.6, −4.4, −4.6.

Sources & evidence

ORD record
ord-1c9b6f8f61e141dba5f59f234fe66eda
Source dataset
uspto-grants-2011_03
Patent number
US07915270B2

Reaction notes

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