Allylchlorodimethylsilane → 2-(4-Allyldimethylsilylphenyl)1,3-dioxolane

HRID 2228386Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[O:12][CH2:11][CH2:10][O:9]2)=[CH:4][CH:3]=1.[C:13]([Li])([CH3:16])(C)[CH3:14].[CH2:18]([Si:21](Cl)(C)[CH3:22])C=C>C1COCC1>[CH2:14]([C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[O:12][CH2:11][CH2:10][O:9]2)=[C:4]([SiH:21]([CH3:22])[CH3:18])[CH:3]=1)[CH:13]=[CH2:16]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 2-(4-bromophenyl)-1,3-dioxolane (2 Scheme 18, 6.0 g, 26.2 mmol) in dried THF (200 mL) at −78° C. was added t-butyllithium (15.4 mL, 1.7 M solution in pentane, 26.2 mmol) over a period of 5 min. After 30 min of further stirring at −78° C., allylchlorodimethylsilane (3.7 g, 27.5 mmol) in THF (20 mL) was added dropwise over a period of 10 min. The reaction mixture was stirred for 1 h and warmed to room temperature. THF was removed under reduced pressure, and the residue was extracted with cold water/ethyl acetate. The organic layer was washed with brine, dried (Na2SO4), and concentrated to give a colorless oil (5.4 g, 91%); 1H NMR (300 MHz, CDCl3) δ 0.31 (s, 6 H), 1.78 (d, J=7.95 Hz, 2 H), 4.02-4.18 (4 H), 4.85 (s, 1 H), 4.90 (m, 1 H), 5.78 (m, 1 H), 5.85 (s, 1 H), 7.50 (d, J=7.95 Hz, 2 H), 7.58 (d, J=7.95 Hz, 2 H); 13C NMR (75 MHz, CDCl3) −3.4 (2C), 23.7, 65.4 (2C), 103.7, 113.6, 125.8 (2C), 133.8 (2C), 134.6, 138.8, 139.9; HRMS calcd for C14H20O2Si 248.1233, found 248.1230.

Workup

stirringThe reaction mixture was stirred for 1 h
temperaturewarmed to room temperature
customTHF was removed under reduced pressure
extractionthe residue was extracted with cold water/ethyl acetate
washThe organic layer was washed with brine
dry with materialdried (Na2SO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-288866f7cc7c4a87b3d15c8a6d578154
Source dataset: uspto-grants-2002_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06416861B1

Reaction notes

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