Methyl 3-bromobenzoate → HCID 16110638, compound

HRID 605627Notes

Reaction equation

HRID 605627 reaction equation
[Si]([O:8][CH:9]([C:22]1[O:23][C:24]([C:27]2[CH:28]=[C:29]([CH:34]=[CH:35][CH:36]=2)[C:30]([O:32][CH3:33])=[O:31])=[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=C(C=CC=1)C(OC)=O>>[C:16]1([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C:9]([C:22]2[O:23][C:24]([C:27]3[CH:28]=[C:29]([CH:34]=[CH:35][CH:36]=3)[C:30]([O:32][CH3:33])=[O:31])=[CH:25][N:26]=2)=[O:8])[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 3

HCID 12070Methyl 3-bromobenzoateHCID 16110606HCID 16110606, compoundHCID 670460482-(1-(Tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole

Product 1

HCID 16110638HCID 16110638, compoundYield 76%

Procedure

Methyl 3-(2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)oxazol-5-yl)benzoate. The title compound was prepared from 2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole (188 mg, 0.284 mmol) and methyl 3-bromobenzoate following General Procedure A. Flash chromatography (2-10% EtOAc/hexanes) yielded the title compound as a clear oil (110 mg, 76%): 1H NMR (CDCl3, 500 MHz) δ 8.40 (m, 1H), 8.07 (d, 1H, J=8.0 Hz), 7.90 (d, 1H, J=8.0 Hz), 7.58 (t, 1H, J=7.6 Hz), 7.44 (s, 1H), 7.35-7.32 (m, 2H), 7.25-7.23 (m, 3H), 4.93 (t, 1H, J=6.0 Hz), 4.03 (s, 3H), 2.67 (t, 2H, J=7.4 Hz), 2.04-1.99 (m, 2H), 1.75-1.68 (m, 2H), 1.45-1.37 (m, 6H), 1.00 (s, 9H), 0.20 (s, 3H), 0.10 (s, 3H); 13C NMR (CDCl3, 125 MHz) δ 166.9, 165.7, 150.6, 143.1, 131.4, 129.7, 129.5, 128.9, 128.8, 128.6, 128.6, 126.1, 125.8, 123.5, 69.1, 52.7, 36.8, 36.4, 31.8, 29.6, 29.6, 26.2, 25.6, 14.1, −4.5, −4.6.

Sources & evidence

ORD record
ord-efda456bed1347d68014a06083dc8ac9
Source dataset
uspto-grants-2011_03
Patent number
US07915270B2

Reaction notes

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