4-Bromoanisole → HCID 16110705, compound

HRID 605619Notes

Reaction equation

HRID 605619 reaction equation
[Si]([O:8][CH:9]([C:22]1[O:23][C:24]([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=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.BrC1C=CC(OC)=CC=1>>[CH3:34][O:33][C:30]1[CH:29]=[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]=1

Participants

4

Reactant 3

HCID 77304-BromoanisoleHCID 16110679HCID 16110679, compoundHCID 670460482-(1-(Tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole

Product 1

HCID 16110705HCID 16110705, compoundYield 84%

Procedure

2-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)-5-(4-methoxyphenyl)oxazole. The title compound was prepared from 2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole (67 mg, 0.101 mmol) and 1-bromo-4-methoxybenzene following General Procedure B. Flash chromatography (5% EtOAc/hexanes) yielded the title compound as a clear oil (41 mg, 84%): 1H NMR (CDCl3, 500 MHz) δ 7.66 (d, 2H, J=9.0 Hz), 7.37-7.34 (m, 3H), 7.27-7.23 (m, 3H), 7.03 (d, 2H, J=9.0 Hz), 4.91 (t, 1H, J=5.5 Hz), 3.93 (s, 3H), 2.68 (t, 2H, J=7.5 Hz), 2.06-1.96 (m, 2H), 1.71-1.68 (m, 2H), 1.46-1.42 (m, 6H), 0.98 (s, 9H), 0.19 (s, 3H), 0.08 (s, 3H); 13C NMR (CDCl3, 125 MHz) δ 164.6, 160.2, 151.6, 143.2, 128.8, 128.7, 126.1, 126.0, 121.3, 120.3, 114.8, 69.1, 55.8, 36.8, 36.3, 31.9, 29.6, 26.2, 26.2, 25.6, 18.7, −4.5, −4.7.

Sources & evidence

ORD record
ord-a10d0205fa0c43a49bc7eb1508e0531d
Source dataset
uspto-grants-2011_03
Patent number
US07915270B2

Reaction notes

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