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

HRID 1749118

反応式

HRID 1749118 の反応式
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]

参加物

6

反応物 4

HCID 1140TolueneHCID 25517Ammonium ChlorideHCID 69795EthyldimethylsilaneHCID 16682930Triethylaluminum

生成物 1

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

試薬・触媒・溶媒 1

HCID 9834912Nickel(II) acetylacetonate触媒

反応条件

温度
0 °C

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-720e2de814034ac3aa3add3b95b456e6
出典データセット
uspto-grants-2015_10
特許番号
US09156770B2

関連ノート

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