Potassium Carbonate → tert-Butyl[(Z)-3-hexene-1,5-diynyl]dimethylsilane
Reaction equation
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]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 23 °C
Procedure
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%).
Workup
- customThe reaction mixture was partitioned between saturated aqueous sodium chloride solution (200 mL) and hexanes (200 mL)
- customThe aqueous layer was separated
- extractionextracted further with hexanes (200 mL)
- dry with materialThe combined organic layers were dried over sodium sulfate
- concentrationwere concentrated
- customThe product was purified by flash column chromatography (hexanes)
Sources & evidence
- ORD record
- ord-5750adfbb19e4abfa738139ca558b9a7
- Source dataset
- uspto-grants-1998_12
- Patent number
- US05849750
Reaction notes
Loading…