tert-Butyldimethylsilyl trifluoromethanesulphonate → 8-(1-((Tert-butyldimethylsilyl)oxy)vinyl)quinoline

HRID 1055939Notes

Reaction equation

[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[C:11](=[O:13])[CH3:12])[CH:4]=[CH:3][CH:2]=1.[Si:14](OS(C(F)(F)F)(=O)=O)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]>C(Cl)Cl.C([O-])(O)=O.[Na+]>[Si:14]([O:13][C:11]([C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[N:1]=[CH:2][CH:3]=[CH:4]2)=[CH2:12])([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 1-(quinolin-8-yl)ethanone (200 mg, 1.169 mmol) and TEA (0.2 mL, 1.520 mmol) in DCM (2 mL) at 0° C. was added TBSOTf (339 mg, 1.286 mmol), and the resulting mixture was stirred at 0° C. for 1 h. The mixture was diluted with sat. aq. NaHCO3 and extracted with EtOAc (2×5 mL). The combined extracts were dried over Na2SO4, filtered, and concentrated in vacuo to yield crude 8-(1-((tert-butyldimethylsilyl)oxy)vinyl)quinoline (300 mg) as a black solid (used without further purification): 1H NMR (400 MHz, DMSO-d6): δ 9.07 (1H, dd, J=1.6 Hz & 2.4 Hz), 8.23 (1H, dd, J=2 Hz & 6.4 Hz), 8.00 (1H, dd, J=1.6 Hz & 5.6 Hz), 7.84 (1H, dd, J=1.6 Hz & 6.8 Hz), 7.59 (1H, t, J=7.6 Hz), 7.49 (1H, dd, J=4 Hz & 4.4 Hz), 5.43 (1H, s), 5.02 (1H, s), 1.01 (9H, s), 0.20 (6H, s). m/z (ESI, +ve) 285.9 (M+H)+.

Workup

extractionextracted with EtOAc (2×5 mL)
dry with materialThe combined extracts were dried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customto yield
customcrude 8-(1-((tert-butyldimethylsilyl)oxy)vinyl)quinoline (300 mg) as a black solid (used without further purification)

Sources & evidence

ORD record: ord-b23e4a2d87ae4fb5a25c7ccc2f2c1432
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394297B2

Reaction notes

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