Sodium borohydride → 2-Tert-butoxy-2-(1-(4-chlorophenyl)-3,6-dimethylnaphthalen-2-yl)acetic acid

Participants

Reaction Steps

2-tert-Butoxy-2-(1-(4-chlorophenyl)-3,6-dimethylnaphthalen-2-yl)acetic acid (58) was prepared with a route similar to that described for compound 53 of Example 51 beginning with 3,6-dimethyl-3,4-dihydronaphthalen-1(2H)-one (prepared from 1-(3-methylphenyl)propan-2-one) and omitting steps 5 and 6 of Example 50, and steps 2 and 5 of Example 51. Step 3 of Example 51 was replaced by treatment with NaBH4 in EtOH at room temperature to afford racemic material. The title compound was isolated (0.075 g) as a white amorphous powder. LCMS-ESI− (m/z): [M−H]− calcd for C24H24ClO3: 395.14; found: 394.96. 1H-NMR: 400 MHz, (CDCl3) δ: 7.69-7.61 (m, 1H); 7.58 (s, 1H); 7.54 (s, 1H); 7.53-7.46 (m, 2H); 7.30-7.23 (m, 1H); 7.21 (d, J=8.4 Hz, 1H); 7.14 (d, J=8.4 Hz, 1H); 5.27 (s, 2H); 2.56 (s, 3H); 2.48 (s, 3H); 1.01 (s, 9H).

Provenance & Evidence