Water → HCID 10965171, compound

Participants

Reaction Conditions

Reaction Steps

Neat DIBAL-H (1.93 mL, 1.52 g, d=0.789, 10.7 mmol, 1.2 equiv) was added to a solution of 1-(1-hexynyl)-1-methylsilacyclobutane (1.62 g, 9,0 mmol) in hexane (14 mL) and Et2O (9 mL) at 0° C. The mixture was stirred for 3 h at 0° C., 9 h at rt, and then was diluted with CH2Cl2 (40 mL). Solid NaF (3.21 g, 76.4 mmol, 8.5 equiv) was added, followed by H2O (2.9 mL, 161 mmol, 17.8 equiv) and the suspension was stirred for 3 h, then was filtered and the filtrate was concentrated in vacuo. The crude product was purified by column chromatography (SiO2, pentane) and Kugelrohr distillation to afford 1.35 g (82%) of (Z)-1 as a colorless oil.

Provenance & Evidence