Trimethylsilylacetylene → HCID 131736482, compound

HRID 1477248Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([CH3:19])([S:15]([CH3:18])(=[O:17])=[O:16])[C:11]([O:13][CH3:14])=[O:12])=[CH:4][CH:3]=1.[C:20]([Si:22]([CH3:25])([CH3:24])[CH3:23])#[CH:21]>C(N(CC)CC)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[CH3:19][C:10]([S:15]([CH3:18])(=[O:17])=[O:16])([CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([C:21]#[C:20][Si:22]([CH3:25])([CH3:24])[CH3:23])=[CH:3][CH:4]=1)[C:11]([O:13][CH3:14])=[O:12]

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirring suspension of methyl 4-(4-bromophenyl)-2-methyl-2-(methylsulfonyl)butanoate (9.3, 6.36 g, 18.23 mmol), bis(triphenylphosphine)palladium(II) chloride (1.28 mg, 1.82 mmol) and copper(I) iodide (347 mg, 1.82 mmol) in triethylamine (30 mL) was added ethynyltrimethylsilane (0.92 mL, 6.49 mmol) and the reaction mixture was heated to 80° C. briefly, and then allowed to stir at room temperature for 18 hr. Volatiles were removed under reduced pressure and the resulting residue was purified by flash chromatography (silica gel/15-50% EtOAc/hexanes) to yield methyl 2-methyl-2-(methylsulfonyl)-4-(4-((trimethylsilyl)ethynyl)phenyl)butanoate (9.4, 4.0 g, 59.9% yield). MS: m/z calcd for C18H26O4SSi 366.13. found [M+H]+ 367.2.

Workup

customVolatiles were removed under reduced pressure
customthe resulting residue was purified by flash chromatography (silica gel/15-50% EtOAc/hexanes)

Sources & evidence

ORD record: ord-94d212b5803743d39e15ed1c8ea5c158
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09403758B2

Reaction notes

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