Potassium Carbonate → tert-Butyl[(Z)-3-hexene-1,5-diynyl]dimethylsilane

HRID 963275노트

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HRID 963275 반응식
C(=O)([O-])[O-].[K+].[K+].[Si:7]([C:14]#[C:15]/[CH:16]=[CH:17]\[C:18]#[C:19][Si](C)(C)C)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8]>CO>[C:10]([Si:7]([C:14]#[C:15]/[CH:16]=[CH:17]\[C:18]#[CH:19])([CH3:9])[CH3:8])([CH3:12])([CH3:13])[CH3:11]

참가 물질

4

반응물 2

HCID 11430Potassium CarbonateHCID 86752751(Z)-1-(tert-butyldimethylsilyl)-6-trimethylsilyl-3-hexen-1,5-diyne

생성물 1

HCID 11033707tert-Butyl[(Z)-3-hexene-1,5-diynyl]dimethylsilane수율 95%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
23 °C

실험 절차

Solid potassium carbonate (5.36 g, 38.9 mmol, 1.10 equiv) was added to a solution of (Z)-1-(tert-butyldimethylsilyl)-6-trimethylsilyl-3-hexen-1,5-diyne (9.26 g, 35.3 mmol, 1 equiv) in methanol (100 mL) at 23° C. and the resulting suspension was stirred at 23° C. for 1 h. The reaction mixture was partitioned between saturated aqueous sodium chloride solution (200 mL) and hexanes (200 mL). The aqueous layer was separated and extracted further with hexanes (200 mL). The combined organic layers were dried over sodium sulfate and were concentrated. The product was purified by flash column chromatography (hexanes) to furnish tert-butyl[(Z)-3-hexene-1,5-diynyl]dimethylsilane (18) as a brown oil (6.35 g, 95%). ##STR30##

후처리

  1. customThe reaction mixture was partitioned between saturated aqueous sodium chloride solution (200 mL) and hexanes (200 mL)
  2. customThe aqueous layer was separated
  3. extractionextracted further with hexanes (200 mL)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. concentrationwere concentrated
  6. customThe product was purified by flash column chromatography (hexanes)

출처 및 근거

ORD 기록
ord-989eb442d2af424a8e351c2ec8302fc7
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05763451

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