3-Ethyl-1-pentyn-3-ol → 2-Tert-butoxy-2-(1-(4-chlorophenyl)-7-(3-ethyl-3-hydroxypent-1-ynyl)-3-methylnaphthalen-2-yl)acetic acid

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2-tert-Butoxy-2-(1-(4-chlorophenyl)-7-(3-ethyl-3-hydroxypent-1-ynyl)-3-methylnaphthalen-2-yl)acetic acid (82) was prepared by the method of Example 67 from ethyl 2-(7-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-tert-butoxyacetate using 3-ethylpent-1-yn-3-ol. 1H-NMR: 400 MHz, (CD3OD) δ: 7.74 (d, J=8 Hz, 1H), 7.67 (s, 1H), 7.58 (m, 3H), 7.40 (d, J=8 Hz, 1H), 7.30 (m, 2H), 5.17 (s, 1H), 2.59 (s, 3H), 1.69 (m, 4H), 1.01 (m, 6H), 0.98 (s, 9H). HPLC (Kinetex 2.6u, 50×4.6 mm, 2-100% MeCN/H2O+0.05% HOAc, 3.5 min run): tR (min)=2.64.

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