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

HRID 1457801ノート

反応式

HRID 1457801 の反応式
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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
23 °C

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-5750adfbb19e4abfa738139ca558b9a7
出典データセット
uspto-grants-1998_12
特許番号
US05849750

反応ノート

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