Hydrochloric Acid → [(4-Isobutylphenyl)ethynyl](trimethyl)silane

HRID 217445

反応式

HRID 217445 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([CH3:11])[CH3:10])=[CH:4][CH:3]=1.[C:12]([Si:14]([CH3:17])([CH3:16])[CH3:15])#[CH:13].Cl>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:8]([C:5]1[CH:6]=[CH:7][C:2]([C:13]#[C:12][Si:14]([CH3:17])([CH3:16])[CH3:15])=[CH:3][CH:4]=1)[CH:9]([CH3:11])[CH3:10]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 66111TrimethylsilylacetyleneHCID 37890181-Bromo-4-(2-methylpropyl)benzene

生成物 1

HCID 58438693[(4-Isobutylphenyl)ethynyl](trimethyl)silane収率 42.5%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

To a solution of Pd(PPh3)4 (542 mg) and TEA (4 mL) in DMF (16 mL) were added 1-bromo-4-isobutylbenzene (1 g) and ethynyl(trimethyl)silane (553 mg) at room temperature, followed by stirring at 60° C. for 4 hours. To the reaction liquid was added 1 M hydrochloric acid, followed by extraction with ether. The insoluble materials were filtered through celite. The organic layer was washed with brine, dried over MgSO4, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane) to obtain [(4-isobutylphenyl)ethynyl](trimethyl)silane (459 mg) as a yellow liquid.

後処理

  1. customTo the reaction liquid
  2. extractionfollowed by extraction with ether
  3. filtrationThe insoluble materials were filtered through celite
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane)

出典と根拠

ORDレコード
ord-f1e45472360443ac87ab58d8f3ec8a95
出典データセット
uspto-grants-2012_06
特許番号
US08193378B2

関連ノート

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