Sodium Sulfate → HCID 59595156, compound

Participants

Reaction Conditions

Reaction Steps

Prepared according to general procedure B using tert-butyl 3-(2-hydroxyphenyl)-3-oxopropanoate (18) (236 mg, 1.0 mmol), p-anisaldehyde (115 μL, 1.0 mmol), 12.0 mL toluene, piperidinium acetate (0.3 mL, 0.025 M in toluene) and sodium sulfate (2.0 g), stirred at 22° C. for 7 d. Purified via recrystallization from hexanes/CH2Cl2, yielding 250 mg (71%) of white crystals. mp=129-132° C.; IR (film) 2982.5; 1708.9; 1603.8; 1246.8; 1155.0 cm−1; 1H NMR (500 MHz, CDCl3) δ 11.97 (bs, 1H); 7.80 (s, 1H); 7.56 (d, J=8.0 Hz, 1H); 7.48 (t, J=7.4 Hz, 1H); 7.32-6.79 (AA′BB′, 4H), 7.04 (t, J=8.6 Hz, 1H), 6.82 (m, 1H), 3.78 (s, 3H); 1.40 (s, 9H); 13C NMR (125 MHz, CDCl3) δ 202.3, 164.1, 162.9, 161.6, 142.0, 137.1, 132.4, 132.0, 128.9, 125.3, 120.2, 119.5, 118.5, 114.7, 82.5, 55.6, 28.1; LRMS (electrospray): Mass calculated for C21H22O5 [M]+, 354.14. Found [M+23]+, 377.5. An NOE difference experiment was conducted for this compound and a positive NOE was seen for the alkene proton when the tert-butyl signal was irradiated and a positive NOE was seen for the tert-butyl signal upon irradiation of the alkene proton.

Provenance & Evidence