Lithium Hydroxide → HCID 56601716, compound

Participants

Reaction Conditions

Reaction Steps

(S)-2-tert-butoxy-2-(3-methyl-1-(spiro[2.5]oct-5-en-6-yl)naphthalen-2-yl)acetic acid was prepared following the procedure for (S)-2-tert-butoxy-2-(1-(4,4-dimethylcyclohex-1-enyl)-3-methylnaphthalen-2-yl)acetic acid of Example 12 except using 4,4,5,5-tetramethyl-2-(spiro[2.5]oct-5-en-6-yl)-1,3,2-dioxaborolane instead of 2-(4,4-dimethylcyclohex-1-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane and that in the final step the reaction was heated to 50° C. overnight followed by an addition of 10 equivalents of lithium hydroxide and heating to 60° C. for four hours and then at 45° C. overnight. 1H-NMR: 400 MHz, (CD3OD) δ: 7.90 (d, J=7.6 Hz, 1H), 7.71 (br d, J=7.2 Hz, 1H), 7.53 (d, J=8.0 Hz, 1H), 7.40 (m, 2H), 5.88 (s, 1H), 5.70 (s, 1H), 2.73 (m, 1H), 2.78 (s, 3H), 2.31 (m, 2H), 2.09 (m, 1H), 1.73 (m, 1H), 1.59 (m, 1H), 1.24 (s, 9H), 0.49 (m, 4H). LCMS-ESI− (m/z): [M−H]−calcd for C25H29O3: 377.22. found: 377.34.

Provenance & Evidence