Regioselective reaction of dilithiated 1-alkynylsilanol with electrophiles

Synlett

Volumn , Issue 10, 1998, Pages 1096-1098

  Uehira, S ^a   Takaku, K ^a   Shinokubo, H ^a   Oshima, K ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002455891     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1898     Document Type: Article

References (29)

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29. Representative experimental procedure: To a THF-suspension (5 mL) of KH (0.8 mmol) was added a solution of 1a (0.19 g, 0.8 mmol) in THF (2 mL) dropwise at 0° C. After 20 min, the mixture was cooled to -78° C, HMPA (0.17 g, 0.96 mmol) and tert-BuLi (0.56 mL, 1.69 M solution in pentane) was added. After being stirred for 1 h at - 78° C, to the resulting yellow solution was added iodomethane (0.57 g, 4.0 mmol). The whole mixture was stirred for another 20 min. Extractive workup (1 N HCl and ethyl acetate) followed by purification by silica-gel column chromatography gave 1-butynyldiphenylsilanol (0.10 g, 0.39 mmol, 49%).