Allylchlorodimethylsilane → Allyldimethyl-[4-(terahydropyran-2-yloxy)-but-1-ynyl]-silane

HRID 1582517Notes

Reaction equation

C([Li])CCC.[CH2:6]([O:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1)[CH2:7][CH:8]=[CH2:9].[CH2:17]([Si:20](Cl)([CH3:22])[CH3:21])[CH:18]=[CH2:19]>C1COCC1>[CH2:17]([Si:20]([CH3:22])([CH3:21])[C:9]#[C:8][CH2:7][CH2:6][O:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1)[CH:18]=[CH2:19]

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of n-butyllithium (12.0 ml, 30 mmol, 2.5 mol dm−3 in hexanes) was added dropwise to a stirred, cooled (−78° C.) solution of compound 2 (4.62 g, 30 mmol) in THF (60 ml) under an atmosphere of dry nitrogen. The reaction mixture was maintained at −78° C. for 1.5 h and a solution of allylchlorodimethylsilane (4.04 g, 30 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 a clear oil. The crude product was purified by column chromatography [silica gel, eluted with hexane/ethyl acetate (4:1), Rf: 0.48]

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 a clear oil
customThe crude product was purified by column chromatography [silica gel, eluted with hexane/ethyl acetate (4:1), Rf: 0.48]

Sources & evidence

ORD record: ord-a225dab37c6a49c692f2e9f0403b1aeb
Source dataset: uspto-grants-2004_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06737124B2

Reaction notes

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