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

HRID 1749118

반응식

HRID 1749118 반응식
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]

참가 물질

6

반응물 4

HCID 1140TolueneHCID 25517Ammonium ChlorideHCID 69795EthyldimethylsilaneHCID 16682930Triethylaluminum

생성물 1

HCID 123973100Ethyldimethyl(((1SR,4RS)-3-methylbicyclo[2.2.1]hept-2-en-2-yl)methyl)silane

시약·촉매·용매 1

HCID 9834912Nickel(II) acetylacetonate촉매

반응 조건

온도
0 °C

실험 절차

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%.

후처리

  1. temperatureto slowly warm to ambient temperature
  2. extractionextracted with ether
  3. washthe combined organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customthe solvents removed in vacuo

출처 및 근거

ORD 기록
ord-720e2de814034ac3aa3add3b95b456e6
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09156770B2

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