o-Iodoanisole → HCID 16110669, compound

HRID 605617Notes

Reaction equation

[Si:1]([O:8][CH:9]([C:22]1[O:23][C:24]([Sn](CCCC)(CCCC)CCCC)=[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:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].I[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=1[O:47][CH3:48]>>[Si:1]([O:8][CH:9]([C:22]1[O:23][C:24]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=2[O:47][CH3:48])=[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:4]([CH3:7])([CH3:5])[CH3:6])([CH3:2])[CH3:3]

Participants

Reactant 2

HCID 68257o-Iodoanisole

HCID 670460482-(1-(Tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole

Product 1

HCID 16110669HCID 16110669, compoundYield 77%

Procedure

The title compound was prepared from 2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole (140 mg, 0.211 mmol) and 1-iodo-2-methoxybenzene following General Procedure A. Flash chromatography (2% EtOAc/hexanes) yielded the title compound as a white solid (78 mg, 77%): 1H NMR (CDCl3, 400 MHz) δ 7.81 (dd, 1H, J=9.2, 6.0 Hz), 7.49 (s, 1H), 7.30-7.27 (m, 3H), 7.19-7.16 (m, 3H), 7.07-7.05 (m, 1H), 6.99 (d, 1H, J=8.4 Hz), 4.85 (t, 1H, J=6.8 Hz), 3.98 (s, 3H), 2.58 (t, 2H, J=8.0 Hz), 1.95-1.91 (m, 2H), 1.63-1.60 (m, 2H), 1.38-1.34 (m, 6H), 0.91 (s, 9H), 0.11 (s, 3H), 0.00 (s, 3H); 13C NMR (CDCl3, 100 MHz) δ 168.8, 160.7, 152.7, 148.0, 134.0, 133.5, 133.3, 131.0, 130.9, 130.7, 125.9, 122.4, 115.9, 73.8, 60.5, 41.6, 41.1, 36.6, 34.3, 34.3, 30.9, 30.3, 23.3, 0.2, 0.0.

Sources & evidence

ORD record: ord-fbbc286195364611bf9a1bc6a754b8ee
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07915270B2

Reaction notes

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