Methanol → HCID 57871421, compound

Participants

Reaction Conditions

Reaction Steps

Add KOH (321 mg, 5.724 mmol) to a mixture of diastereomeric isomer pair 1 of 6-{1-ethyl-1-[4-(1-ethyl-2-hydroxy-3,3-dimethyl-butoxy)-3-methyl-phenyl]propyl}-naphthalene-2-carboxylic acid methyl ester (702 mg, 1.431 mmol), THF (9 ml), MeOH (3 ml), and H2O (1 ml). Heat the reaction mixture to 60° C. and stir it for 14 h. Cool and partition the reaction mixture between Et2O and 1N HCl. Dry the organic layer over MgSO4, filter, and concentrate the filter in vacuo to give the title compound as a glassy solid (665 mg, 97%). 1NMR (400 MHz, CDCl3) δ ppm: 0.64 (t, J=7.6 Hz, 6H), 0.93 (t, J=8.4 Hz, 3H), 0.93 (s, 9H), 1.72 (m, 1H), 1.82 (m, 1H), 2.12 (s, 3H), 2.19 (q, 4H), 3.28 (s, 1H), 4.28 (dd, J=6.0, 3.2 Hz, 1H), 6.65 (d, J=8.4 Hz, 1H), 6.90 (d, J=2.0 Hz, 1H), 6.94 (dd, J=6.0, 2.4 Hz, 1H), 7.21 (dd, J=7.2, 1.6 Hz, 1H), 7.78 (d, J=8.8 Hz, 1H), 7.86 (s, 1H), 7.89 (d, J=8.8 Hz, 1H), 8.09 (dd, J=6.8, 1.6 Hz, 1H), 8.62 (s, 1H). High Res. ES-MS: 499.2832; calc. for C31H40O4+Na: 499.2825.

Provenance & Evidence