Trifluoroacetic acid → HCID 86653779, compound

Participants

Reaction Steps

1-(2,5-Bis(benzyloxy)-3,4,6-trimethylphenyl)but-3-en-1-ol (3.7 g, 9.4 mmol) was dissolved into 10 mL CH2Cl2 and treated with Et3SiH (12 mL, 94.4 mmol.). To this clear, colorless solution was added trifluoroacetic acid (TFA) (10.5 mL, 142 mmol) neat over 3 minutes which darkened the solution and exothermed. The reaction vessel was placed in a room temperature water bath and let stir for 1.25 h. The reaction was concentrated to yellow oil via rotary evaporation and the residue dissolved in 100 mL methyl t-butyl ether (MTBE). To this was added 50 mL 2.5 M K2CO3, the layers separated and the aqueous phase extracted 3×50 mL MTBE. The combined organics were washed with 50 mL saturated aqueous NaCl, dried over Na2SO4 and concentrated to give 1-(2,5-bis(benzyloxy)-3,4,6-trimethylphenyl)-3-butene, (3.6 g) as a yellow oil. 1H NMR (400 MHz, CDCl3) δ=7.51 (d, 4 H), 7.44-7.35 (m, 6 H), 5.90 (m, 1 H), 5.06 (d, 1 H), 4.97 (d, 1 H), 4.78 (s, 2 H), 4.74 (s, 2 H), 2.74 (m, 2 H), 2.27-2.24 (m, 9 H) ppm.

Provenance & Evidence