1,2-Dichlorobenzene → (2R,2'S,3'R,4'S,5'S,6'R)-6-chloro-5-(4-ethylbenzyl)-6'-(hydroxymethyl)-2-methoxy-3',4',5',6'-tetrahydro-2H-spiro[benzofuran-3,2'-pyran]-3',4',5'-triol

Participants

Reaction Steps

To a solution of 54 (22 mg, 27 μmol) in a mixture of MeOH (1.5 mL) and THF (0.5 mL) were added Pd(OH)2/C (15 mg) and 1,2-dichlorobenzene (20 μL). A balloon of hydrogen gas was attached for 0.5 h with vigorous stirring. LC/MS indicated that de-protection was complete. The reaction mixture was filtered through Celite, concentrated to a residue, and purified by preparatory TLC (5% MeOH in DCM) to give 55 (9.3 mg, 76%). 1H NMR (300 MHz, CD3OD) δ 7.20 (s, 1H), 7.06 (s, 4H), 6.82 (s, 1H), 5.61 (s, 1H), 3.99 (s, 2H), 3.63-3.79 (m, 3H), 3.55 (s, 3H), 3.42-3.60 (m, 3H), 2.57 (q, J=7.5 Hz, 2H), 1.19 (t, J=7.5 Hz, 3H). LCMS m/z 451 (M+H), 473 (M+Na).

Provenance & Evidence