Methyl 4-bromobenzoate → HCID 16110644, compound

HRID 605628Notes

Reaction equation

HRID 605628 reaction equation
[Si]([O:8][CH:9]([C:22]1[O:23][C:24]([C:27]2[CH:36]=[CH:35][C:30]([C:31]([O:33][CH3:34])=[O:32])=[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(C(OC)=O)=CC=1>>[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:36]=[CH:35][C:30]([C:31]([O:33][CH3:34])=[O:32])=[CH:29][CH:28]=3)=[CH:25][N:26]=2)=[O:8])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 3

HCID 12081Methyl 4-bromobenzoateHCID 16110612HCID 16110612, compoundHCID 670460482-(1-(Tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole

Product 1

HCID 16110644HCID 16110644, compoundYield 68%

Procedure

Methyl 4-(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 (85 mg, 0.128 mmol) and methyl 4-bromobenzoate following General Procedure A. Flash chromatography (2-10% EtOAc/hexanes) yielded the title compound as a clear oil (44 mg, 68%): 1H NMR (CDCl3, 500 MHz) δ 8.17 (d, 2H, J=8.5 Hz), 7.77 (d, 2H, J=8.5 Hz), 7.47 (s, 1H), 7.36-7.33 (m, 2H), 7.26-7.23 (m, 3H), 4.93 (t, 1H, J=6.0 Hz), 4.02 (s, 3H), 2.67 (t, 2H, J=7.5 Hz), 2.05-1.97 (m, 2H), 1.75-1.68 (m, 2H), 1.47-1.40 (m, 6H), 0.99 (s, 9H), 0.19 (s, 3H), 0.09 (s, 3H); 13C NMR (CDCl3, 125 MHz) δ 166.9, 166.2, 150.6, 143.2, 132.5, 130.7, 130.0, 128.8, 128.6, 126.0, 124.3, 124.1, 69.1, 52.6, 36.8, 36.3, 31.8, 29.6, 26.2, 26.2, 25.5, 18.6, −4.5, −4.7.

Sources & evidence

ORD record
ord-48b7a4a692424d9da1ac8c5a051b57eb
Source dataset
uspto-grants-2011_03
Patent number
US07915270B2

Reaction notes

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