Tetrahydrofuran → HCID 117899644, compound

HRID 522457Notes

Reaction equation

O1CCCC1.[S:6]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][C:16]1[CH:21]=[C:20]([S:22][CH2:23][C:24]([F:27])([F:26])[F:25])[C:19]([CH3:28])=[CH:18][C:17]=1[CH3:29])C#N.[F:30][C:31]([Si](C)(C)C)([F:33])[F:32].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C(OCC)(=O)C.CCCCCC>[F:30][C:31]([F:33])([F:32])[S:6][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][C:16]1[CH:21]=[C:20]([S:22][CH2:23][C:24]([F:27])([F:25])[F:26])[C:19]([CH3:28])=[CH:18][C:17]=1[CH3:29]

Participants

Conditions

Temperature: 0 °C

Procedure

To 100 ml of tetrahydrofuran were added 1.37 g (3.63 mmol) of 6-thiocyanatohexyl-[2,4-dimethyl-5-(2,2,2-trifluoroethylthio)phenyl]ether and 1.29 g (9.07 mmol) of trifluoromethyltrimethylsilane. Thereto was added 0.4 ml (0.4 mmol) of tetrahydrofuran solution of tetra-n-butylammonium fluoride (1 mol/liter) at 0° C., and the mixture was stirred for 4 hours at 0° C. Then, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent: a mixed solvent of n-hexane:ethyl acetate=20:1), to obtain 1.36 g (yield: 89%) of an intended product.

Workup

distillationThen, the solvent was distilled off under reduced pressure
customthe residue was purified by silica gel column chromatography (

Sources & evidence

ORD record: ord-13e56e14b1ad4d869419144c5ce1c56c
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09332754B2

Reaction notes

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