1-(3-chlorophenyl)-2,2,2-trifluoroethanone → HCID 16110702, compound

HRID 605609Notes

Reaction equation

HRID 605609 reaction equation
[Si]([O:8][CH:9]([C:22]1[O:23][C:24]([C:27]2[CH:28]=[C:29]([C:33](=[O:38])[C:34]([F:37])([F:36])[F:35])[CH:30]=[CH:31][CH:32]=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.ClC1C=C(C(=O)C(F)(F)F)C=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:32]=[CH:31][CH:30]=[C:29]([C:33](=[O:38])[C:34]([F:37])([F:35])[F:36])[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 27579311-(3-chlorophenyl)-2,2,2-trifluoroethanoneHCID 16110610HCID 16110610, compoundHCID 670460482-(1-(Tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole

Product 1

HCID 16110702HCID 16110702, compoundYield 87%

Procedure

1-(3-(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 (37 mg, 0.056 mmol) and 1-(3-chlorophenyl)-2,2,2-trifluoroethanone following General Procedure B. Flash chromatography (5-20% EtOAc/hexanes) yielded the title compound as a clear oil (26 mg, 87%): 1H NMR (CDCl3, 600 MHz) δ 8.31 (s, 1H), 8.01-7.94 (m, 2H), 7.61 (t, 1H, J=7.2 Hz), 7.38 (s, 1H), 7.27-7.24 (m, 2H), 7.16-7.14 (m, 3H), 4.84 (t, 1H, J=6.0 Hz), 2.58 (t, 2H, J=7.5 Hz), 1.95-1.88 (m, 2H), 1.64-1.55 (m, 2H), 1.37-1.34 (m, 6H), 0.90 (s, 9H), 0.10 (s, 3H), 0.00 (s, 3H); 13C NMR (CDCl3, 150 MHz) δ 181.0 (d, J=35 Hz), 166.7, 150.2, 143.6, 131.5, 130.7, 130.4, 130.2, 129.2, 129.1, 129.0, 126.4, 126.2, 124.0, 117.7 (d, J=289 Hz), 69.5, 37.2, 36.8, 32.3, 30.0, 26.6, 26.6, 26.0, 19.1, −4.1, −4.2.

Sources & evidence

ORD record
ord-7e2b4fd741f94e799c257315fe544ff6
Source dataset
uspto-grants-2011_03
Patent number
US07915270B2

Reaction notes

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