Toluene → Ethyldimethyl(((1SR,4RS)-3-methylbicyclo[2.2.1]hept-2-en-2-yl)methyl)silane

HRID 1749118Notes

Reaction equation

C([Al]([CH2:6][CH3:7])CC)C.[CH3:8][SiH:9]([CH3:12])[CH2:10][CH3:11].[Cl-].[NH4+].[C:15]1([CH3:21])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.[Ni+2]>[CH2:10]([Si:9]([CH3:12])([CH3:8])[CH2:19][C:20]1[CH:7]2[CH2:6][CH:16]([C:15]=1[CH3:21])[CH2:17][CH2:18]2)[CH3:11]

Participants

Conditions

Temperature: 0 °C

Procedure

Triethyl aluminium (1.0 M in hexanes, 4.2 mL, 4.2 mmol) was added slowly dropwise to a suspension of Ni(acac)2 (dried in vacuo 120° C. 3 hrs, 107 mg, 0.4 mmol, 5 mol %), santadiene (1.0 g, 8.3 mmol) in freshly degassed toluene (85 mL) cooled to 0° C. After 15 minutes, dimethyl ethyl silane (1.1 mL, 8.3 mmol) was added slowly dropwise and the solution was then allowed to slowly warm to ambient temperature and stirred for a further 2 hours. The reaction mixture was poured into saturated ammonium chloride solution and extracted with ether, then the combined organic phase was washed with brine and dried over Na2SO4, then filtered and the solvents removed in vacuo to yield the crude allyl silane 0.9 g, which was further purified by bulb to bulb distillation 30° C. at 0.08 mbar and gave the desired ally silane 0.65 g, 37%.

Workup

temperatureto slowly warm to ambient temperature
extractionextracted with ether
washthe combined organic phase was washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
customthe solvents removed in vacuo

Sources & evidence

ORD record: ord-720e2de814034ac3aa3add3b95b456e6
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156770B2

Reaction notes

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