Hexane → HCID 54509049, compound

Participants

Reaction Steps

Lithium hydroxide monohydrate (22.55 g, 0.54 mol) was added in one portion to a solution of 21.62 g (82.38 mmol) silyl diynene (compound N of step (b)) in 240 mL tetrahydrofuran and 40 mL water stirring at 25° C. The reaction was stirred for 1.58h and then diluted with 1:1 ether:hexane and water. The aqueous layer was reextracted with three portions of ether and then the combined organic extracts were dried over anhydrous sodium sulfate. Flash chromatography over silica gel using a gradient of 2.5 to 10% ethyl acetate/hexane as eluent provided 15.69 g (98%) of brown liquid:

Provenance & Evidence