[CH2:1](O)[C:2]#[CH:3].C(Cl)Cl.CCN(CC)CC.[C:15](Cl)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[OH2:24]>CN(C1C=CN=CC=1)C>[C:15]([O:22][CH2:3][C:2]#[CH:1])(=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1
To a solution of prop-2-yn-1-ol (3.63 mL, 62.4 mmol), DCM (180 mL), and Et3N (17.40 mL, 125 mmol) at 0° C. were added benzoyl chloride (7.25 mL, 62.4 mmol) and DMAP (0.381 g, 3.12 mmol). The reaction was stirred while warming to room temperature overnight. The reaction was diluted with water and the layers separated. The aqueous was extracted with DCM and the combined organics were dried over Na2SO4, filtered, and concentrated to afford prop-2-yn-1-yl benzoate which was used in subsequent reactions without further purification. LC/MS m/z 161 [M+H]+.
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