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

HRID 217445

반응식

HRID 217445 반응식
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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-f1e45472360443ac87ab58d8f3ec8a95
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193378B2

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