Methyl 5-bromofuran-2-carboxylate → HCID 16110660, compound

HRID 605663Notes

Reaction equation

HRID 605663 reaction equation
[Si]([O:8][CH:9]([C:22]1[O:23][C:24]([C:27]2[O:31][C:30]([C:32]([O:34][CH3:35])=[O:33])=[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.BrC1OC(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[O:31][C:30]([C:32]([O:34][CH3:35])=[O:33])=[CH:29][CH:28]=3)=[CH:25][N:26]=2)=[O:8])[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 3

HCID 599633Methyl 5-bromofuran-2-carboxylateHCID 16110628HCID 16110628, compoundHCID 670460482-(1-(Tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole

Product 1

HCID 16110660HCID 16110660, compoundYield 99%

Procedure

Methyl 5-(2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)oxazol-5-yl)furan-2-carboxylate. The title compound was prepared from 2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole (82 mg, 0.125 mmol) and methyl 5-bromofuran-2-carboxylate following General Procedure A. Flash chromatography (2-10% EtOAc/hexanes) yielded the title compound as a clear oil (62 mg, 99%): 1H NMR (CDCl3, 400 MHz) δ 7.42 (s, 1H), 7.29-7.25 (m, 3H), 7.19-7.16 (m, 3H), 6.70 (d, 1H, J=3.6 Hz), 4.83 (t, 1H, J=6.0 Hz), 3.92 (s, 3H), 2.60 (t, 2H, J=7.6 Hz), 1.96-1.85 (m, 2H), 1.71-1.57 (m, 2H), 1.40-1.33 (m, 6H), 0.90 (s, 9H), 0.10 (s, 3H), 0.00 (s, 3H); 13C NMR (CDCl3, 100 MHz) δ 163.8, 151.9, 149.1, 147.8, 147.5, 133.4, 133.2, 130.6, 129.3, 124.6, 113.6, 113.5, 73.6, 57.1, 41.3, 40.9, 36.4, 34.1, 30.7, 30.7, 30.1, 23.2, 0.0, −0.1.

Sources & evidence

ORD record
ord-8ce82906b8b2466a9534236358470b78
Source dataset
uspto-grants-2011_03
Patent number
US07915270B2

Reaction notes

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