[O:1]([CH2:8][CH2:9][CH2:10][C:11]#[CH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[C:15]1(O)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[H][H].ClCCCC#C.[O:30]1CCC[CH2:31]1>CCCCCC.O.CN(C)P(=O)(N(C)C)N(C)C>[O:1]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:18]1[CH:19]=[CH:20][C:15]([CH2:31][OH:30])=[CH:16][CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=15-Phenoxypent-1-yne--The process described by the Swiss patent [Chem. Abstr. 93: 167896d) was used. Thus, a mixture of 2.8 g sodium hydride, 5.51 g phenol in 40 mL dry tetrahydrofuran (THF) was stirred at 0° C. under argon until hydrogen evolution ceased. To the resultant solution was added 10 mL dry hexamethylphosphoric triamide (HMPA) followed by a solution containing 5-chloropent-1-yne (4.85 g) in 5 mL THF. The solution was heated at 80° C. for 3 days. The cooled (ambient temperature) mixture was diluted with n-hexane and water. The hexane layer was washed with 2×50 mL portions of water, 1×10 mL 10% potassium carbonate and dried (MgSO4). The evaporated extract was distilled (bp 115°-118° C., 23 mm) to give the title compound (69%) as a colorless oil.
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