Benzoic acid, 2-iodo-, methyl ester → HCID 16110694, compound

HRID 605626Notes

Reaction equation

HRID 605626 reaction equation
[Si]([O:8][CH:9]([C:22]1[O:23][C:24]([C:27]2[CH:36]=[CH:35][CH:34]=[CH:33][C:28]=2[C:29]([O:31][CH3:32])=[O:30])=[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.IC1C=CC=CC=1C(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:36]=[CH:35][CH:34]=[CH:33][C:28]=3[C:29]([O:31][CH3:32])=[O:30])=[CH:25][N:26]=2)=[O:8])[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 3

HCID 69132Benzoic acid, 2-iodo-, methyl esterHCID 16110600HCID 16110600, compoundHCID 670460482-(1-(Tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole

Product 1

HCID 16110694HCID 16110694, compoundYield 99%

Procedure

Methyl 2-(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 (166 mg, 0.251 mmol) and methyl 2-iodobenzoate following General Procedure A. Flash chromatography (2-20% EtOAc/hexanes) yielded the title compound as a clear oil (125 mg, 99%): 1H NMR (CDCl3, 400 MHz) δ 7.75 (d, 1H, J=7.6 Hz), 7.62 (d, 1H, J=8.0 Hz), 7.53 (t, 1H, J=7.6 Hz), 7.41 (t, 1H, J=7.6 Hz), 7.28-7.24 (m, 3H), 7.17-7.15 (m, 3H), 4.83 (t, 1H, J=6.8 Hz), 3.85 (s, 3H), 2.60 (t, 2H, J=7.4 Hz), 1.92-1.90 (m, 2H), 1.64-1.60 (m, 2H), 1.38-1.33 (m, 6H), 0.90 (s, 9H), 0.11 (s, 3H), 0.00 (s, 3H); 13C NMR (CDCl3, 100 MHz) δ 173.5, 170.3, 154.6, 147.9, 136.5, 135.1, 135.0, 134.9, 133.7, 133.5, 133.4, 132.3, 130.7, 129.8, 73.8, 57.6, 41.6, 41.1, 36.6, 34.3, 34.3, 30.9, 30.1, 23.4, 0.2, 0.0.

Sources & evidence

ORD record
ord-8887396a42a24f95a4e4ed8231f5c173
Source dataset
uspto-grants-2011_03
Patent number
US07915270B2

Reaction notes

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