3-Iodophenol → HCID 16110640, compound

HRID 605635Notes

Reaction equation

HRID 605635 reaction equation
[Si]([O:8][CH:9]([C:22]1[O:23][C:24]([C:27]2[CH:28]=[C:29]([OH:33])[CH:30]=[CH:31][CH:32]=2)=[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=C(O)C=CC=1>>[OH:33][C:29]1[CH:28]=[C:27]([C:24]2[O:23][C:22]([C:9](=[O:8])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[N:26][CH:25]=2)[CH:32]=[CH:31][CH:30]=1

Participants

4

Reactant 3

HCID 122723-IodophenolHCID 16110608HCID 16110608, compoundHCID 670460482-(1-(Tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole

Product 1

HCID 16110640HCID 16110640, compoundYield 41%

Procedure

3-(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 (99 mg, 0.149 mmol) and 3-iodophenol following General Procedure A. Flash chromatography (10-30% EtOAc/hexanes) yielded the title compound as a clear oil (29 mg, 41%): 1H NMR (CDCl3, 500 MHz) δ 7.79-7.77 (m, 1H), 7.62 (s, 1H), 7.56 (br s, 1H), 7.39-7.35 (m, 2H), 7.29-7.24 (m, 4 H), 7.09-7.04 (m, 2H), 4.95 (t, 1H, J=6.0 Hz), 2.65 (t, 2H, J=7.5 Hz), 2.05-1.95 (m, 2H), 1.67-1.64 (m, 2H), 1.47-1.34 (m, 6H), 0.97 (s, 9H), 0.17 (s, 3H), 0.07 (s, 3H); 13C NMR (CDCl3, 125 MHz) δ 164.3, 153.1, 148.8, 143.2, 129.7, 128.8, 128.6, 126.5, 126.0, 124.8, 121.0, 116.8, 115.6, 69.0, 37.0, 36.3, 31.8, 30.1, 26.2, 26.2, 25.5, 18.6, −4.5, −4.7.

Sources & evidence

ORD record
ord-d096992228994f6383e3c74426868ff6
Source dataset
uspto-grants-2011_03
Patent number
US07915270B2

Reaction notes

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