4-Iodophenylacetate → 1-(5-(4-Hydroxyphenyl)oxazol-2-yl)-7-phenylheptan-1-one

HRID 605637

Reaction equation

HRID 605637 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:15][C:14]([CH:16]([O:29][Si](C(C)(C)C)(C)C)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[N:13][CH:12]=2)=[CH:7][CH:6]=1)(=O)C.[Si](OC(C1OC([Sn](CCCC)(CCCC)CCCC)=CN=1)CCCCCCC1C=CC=CC=1)(C(C)(C)C)(C)C.C(OC1C=CC(I)=CC=1)(=O)C>>[OH:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[O:15][C:14]([C:16](=[O:29])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)=[N:13][CH:12]=2)=[CH:9][CH:10]=1

Participants

4

Reactant 3

HCID 1417934-IodophenylacetateHCID 670460444-(2-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)oxazol-5-yl)phenyl acetateHCID 670460482-(1-(Tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole

Product 1

HCID 161106461-(5-(4-Hydroxyphenyl)oxazol-2-yl)-7-phenylheptan-1-oneYield 54%

Procedure

4-(2-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)oxazol-5-yl)phenyl acetate. The title compound was prepared from 2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole (74 mg, 0.112 mmol) and 4-iodophenyl acetate following General Procedure A. Flash chromatography (5-20% EtOAc/hexanes) yielded the title compound as a clear oil (31 mg, 54%): 1H NMR (CDCl3, 600 MHz) δ 7.65 (d, 2H, J=7.8 Hz), 7.27-7.24 (m, 3H), 7.16-7.14 (m, 5H), 4.82 (t, 1H, J=6.0 Hz), 2.58 (t, 2H, J=7.5 Hz), 2.32 (s, 3H), 1.97-1.87 (m, 2H), 1.65-1.60 (m, 2H), 1.45-1.34 (m, 6H), 0.89 (s, 9H), 0.09 (s, 3H), −0.02 (s, 3H); 13C NMR (CDCl3, 150 MHz) δ 170.2, 165.8, 151.4, 151.3, 143.7, 129.2, 129.1, 126.7, 126.4, 126.2, 123.1, 122.4, 69.5, 37.3, 36.8, 32.3, 30.0, 26.6, 26.6, 26.0, 22.1, 19.1, −4.1, −4.2.

Sources & evidence

ORD record
ord-68dd3b34b1034d23920e0873226bdbb3
Source dataset
uspto-grants-2011_03
Patent number
US07915270B2

Linked notes

Loading…