Ethanol → HCID 18614932, compound

Participants

Reaction Steps

A solution of 4-[(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-anthracen-1-yl)-hydroxymethyl]-benzoic acid (from Example 37, 30 mg, 0.07 mmol) in dichloromethane (5 mL) was treated with excess triethylsilane (0.2 mL) and BF3-Et2O (0.16 mL) at 0° C. The solution was allowed to stir for 10 min and then EtOH was added. The mixture was diluted with water and EtOAc. The organic solution was washed with water and brine, dried (Na2SO4), filtered, and concentrated to yield 4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-anthracen-1-ylmethyl)-benzoic acid (139) 15 mg (55%) as a colorless oil: 1H NMR (400 MHz, CDCl3) δ 8.01(½ABq, J=8.2 Hz, 2H, ArH), 7.81(s, 1H, ArH), 7,77(s, 1H, ArH), 7.66(d, J=8.2 Hz, 1H, ArH), 7.32(m, 3H, ArH), 7.24(s, 1H, ArH), 7.19(d, J=6.7 Hz, 1H, ArH), 4.45(s, 2H, CH2), 1.72(m, 4H, 2CH2), 1.35(s, 6H, 2CH3), 1.24(s, 6H, 2CH3).

Provenance & Evidence