Pinacolone → 3-[3-Methyl-4(2-hydroxy-3,3-dimethylbutoxy)phenyl]-3-[3-methyl-4-(3,3-dimethyl-2-oxobutoxy)phenyl]pentane

Participants

Reaction Steps

To a solution of the compound of example 7 (100 mg, 0.26 mmol) in DMF (2.5 mL) was added NaH (7.0 mg, 0.29 mmol). The reaction mixture was stirred at ambient temperature for 30 min, then pinacolone (39 mg, 0.29 mmol) was added. The reaction was stirred at ambient temperature for I h or until judged complete by TLC (20% ethyl acetate in hexanes). The reaction mixture was quenched with water, and diluted with ethyl acetate. The organic fraction was separated, washed with water and brine, dried over MgSO4, and concentrated in vacuo. Chromatography (silica, 10% ethyl acetate in hexanes) afforded 117 mg (0.24 mmol, 92%) of 11. 1HNMR (CDCl3) δ: 6.91 (m, 4 H, Ar—H), 6.69 (d, J=8.3 Hz, 1 H, Ar—H), 6.49 (d, J=8.3 Hz, 1 H, Ar—H), 4.83 (s, 2 H, CH2), 4.09 (dd, J=11.3 Hz, J=3.3 Hz, 1 H, CH2), 3.85 (t, J=11.3 Hz, 1 H, CH2), 3.69 (d, J=11.3 Hz, 1 H, CH2), 2.23 (s, 3 H), Ar—CH3), 2.18 (s, 3 H, Ar—CH3), 2.00 (q, J=7.3 Hz, 4 H, CH2CH3), 1.24 (s, 9 H, t-Bu), 1.00 (s, 9 H, t-Bu), 0.58 (t, J=7.3 Hz, 6 H, CH2CH3).

Provenance & Evidence