[H-].[Na+].[OH:3][CH2:4][C:5]#[C:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][CH2:15][OH:16])=[CH:9][CH:8]=1.Br[CH2:18][C:19]([O:21][CH3:22])=[O:20].[NH4+].[Cl-]>C1COCC1>[C:19]([CH2:18][O:3][CH2:4][C:5]#[C:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][CH2:15][O:16][CH2:18][C:19]([O:21][CH3:22])=[O:20])=[CH:9][CH:8]=1)([OH:21])=[O:20]
A 60% suspension of NaH (2.1 g, 53.7 mmol) is added to a solution of 3-[4-(3-hydroxyprop-1-ynyl)-phenyl]prop-2-yn-1-ol (A6, 0.5 g, 2.68 mmol) in absolute THF (20 ml), and the mixture is stirred at 70° C. for 2 h. After cooling to RT, methyl bromoacetate (5.2 ml, 53.7 mmol) is added dropwise to the reaction solution, and the mixture is stirred at RT overnight. For work-up, the reaction solution is poured into an ice-cooled semisaturated aqueous NH4Cl solution (25 ml) and extracted (2×) with ethyl acetate. The combined organic phases are dried over MgSO4, filtered off and concentrated under reduced pressure. The title compound (0.88 g) is obtained as a colorless powder. TLC, silica gel, glass plates, [Tol/Ac (7:3)], Rf=0.70.
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