Allylchlorodimethylsilane → HCID 131723382, compound

HRID 2228390Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH3:13])[O:12][CH2:11][CH2:10][O:9]2)=[CH:4][CH:3]=1.[C:14]([Li])([CH3:17])(C)[CH3:15].[CH2:19]([Si:22](Cl)(C)[CH3:23])C=C>C1COCC1>[CH2:15]([C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH3:13])[O:12][CH2:11][CH2:10][O:9]2)=[C:4]([SiH:22]([CH3:23])[CH3:19])[CH:3]=1)[CH:14]=[CH2:17]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 2-(4-bromophenyl)-2-methyl-1,3-dioxolane (22, 22.0 g, 90 mmol) in dried THF (600 mL) at −78° C. was added t-butyllithium (53.0 mL, 1.7 M solution in pentane, 90 mmol) over a period of 15 min. After 30 min of further stirring at −78° C., allylchlorodimethylsilane (12.2 g, 90 mmol) in THF (40 mL) was added dropwise over a period of 20 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 H2/ethyl acetate. The organic layer was washed with brine, dried (Na2SO4), and concentrated to give a colorless oil (19.8 g, 91%); 1H NMR (300 MHz, CDCl3) δ 0.30 (s, 6 H), 1.68 (s, 3 H), 1.77 (d, J=8.01 Hz, 2 H), 3.80 (m, 2 H), 4.06 (m, 2 H), 4.86 (m, 1 H), 4.90 (m, 1 H), 5.80 (ddt, J=16.89, 10.23, 8.07 Hz, 1 H), 7.47-7.52 (4 H)); 13C NMR (75 MHz, CDCl3) −3.3 (2C), 23.7, 27.6, 64.5 (2C), 108.8, 113.5, 124.6 (2C), 133.6 (2C), 134.6, 138.2, 144.1.

Workup

stirringThe reaction mixture was stirred for 1 h
temperaturewarmed to room temperature
customTHF was removed under reduced pressure
extractionthe residue was extracted with H2/ethyl acetate
washThe organic layer was washed with brine
dry with materialdried (Na2SO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-d00049fa91094d14bb05c95864fcadc8
Source dataset: uspto-grants-2002_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06416861B1

Reaction notes

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