Silane, chlorodimethyl(3,3,3-trifluoropropyl)- → HCID 22717494, compound

HRID 1582516Notes

Reaction equation

C([Li])CCC.[CH2:6]([O:9][CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][O:11]1)[C:7]#[CH:8].Cl[Si:17]([CH3:25])([CH3:24])[CH2:18][CH2:19][C:20]([F:23])([F:22])[F:21]>C1COCC1>[CH3:24][Si:17]([CH3:25])([C:8]#[C:7][CH2:6][O:9][CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][O:11]1)[CH2:18][CH2:19][C:20]([F:23])([F:22])[F:21]

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of n-butyllithium (12.0 ml, 30.0 mmol, 2.5 mol dm−3 in hexanes) was added dropwise to a stirred, cooled (−78° C.) solution of compound 1 (4.20 g, 30.0 mmol) in THF (80 ml) under an atmosphere of dry nitrogen. The reaction mixture was maintained at −78° C. for 1.5 h and a solution of chlorodimethyl-3,3,3-trifluoropropylsilane (5.72 g, 30.0 mmol) in THF (20 ml) added dropwise. The reaction mixture was allowed to warm to room temperature, washed with water and the organic layer extracted into ethyl acetate/hexane (3 times). The combined extracts were washed with brine, dried (MgSO4) and the solvent removed in vacuo to yield an amber oil. The crude product was purified by column chromatography [silica gel, eluted with hexane/ethyl acetate (4:1), Rf: 0.58] to yield a colorless oil.

Workup

temperatureto warm to room temperature
washwashed with water
extractionthe organic layer extracted into ethyl acetate/hexane (3 times)
washThe combined extracts were washed with brine
dry with materialdried (MgSO4)
customthe solvent removed in vacuo
customto yield an amber oil
customThe crude product was purified by column chromatography [silica gel, eluted with hexane/ethyl acetate (4:1), Rf: 0.58]
customto yield a colorless oil

Sources & evidence

ORD record: ord-1e97f0f366d94e9e9682ff2815cc031d
Source dataset: uspto-grants-2004_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06737124B2

Reaction notes

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