HCID 16110604, compound → HCID 16110697, compound

HRID 605608Notes

Reaction equation

HRID 605608 reaction equation
[Si]([O:8][CH:9]([C:22]1[O:23][C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[C:33](=[O:38])[C:34]([F:37])([F:36])[F:35])=[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.ClC1C=CC=CC=1C(=O)C(F)(F)F>>[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:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:33](=[O:38])[C:34]([F:37])([F:35])[F:36])=[CH:25][N:26]=2)=[O:8])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 3

HCID 16110604HCID 16110604, compoundHCID 216456581-(2-Chlorophenyl)-2,2,2-trifluoroethan-1-oneHCID 670460482-(1-(Tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole

Product 1

HCID 16110697HCID 16110697, compoundYield 83%

Procedure

1-(2-(2-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)oxazol-5-yl)phenyl)-2,2,2-trifluoroethanone. The title compound was prepared from 2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole (63 mg, 0.095 mmol) and 1-(2-chlorophenyl)-2,2,2-trifluoroethanone following General Procedure B. Flash chromatography (2-10% EtOAc/hexanes) yielded the title compound as a clear oil (43 mg, 83%): 1H NMR (CDCl3, 600 MHz) δ 7.70-7.64 (m, 3H), 7.51-7.48 (m, 1H), 7.26-7.24 (m, 3H), 7.16-7.15 (m, 3H), 4.79 (t, 1H, J=6.0 Hz), 2.58 (t, 2H, J=7.5 Hz), 1.88-1.81 (m, 2H), 1.61-1.60 (m, 2H), 1.35-1.25 (m, 6H), 0.87 (s, 9H), 0.07 (s, 3H), −0.05 (s, 3H); 13C NMR (CDCl3, 150 MHz) δ 186.2 (d, J=35 Hz), 167.0, 149.4, 143.7, 133.6, 133.6, 131.1, 129.5, 129.4, 129.3, 129.1, 128.3, 126.4, 125.6, 116.4 (d, J=285 Hz), 69.4, 37.3, 36.8, 32.3, 30.0, 26.5, 26.5, 25.8, 19.0, −4.2, −4.4.

Sources & evidence

ORD record
ord-c0009c05fb10417c83d98d4d6e82b61d
Source dataset
uspto-grants-2011_03
Patent number
US07915270B2

Reaction notes

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