Potassium Sodium Tartrate → (S)-2-(1-(1-chloro-3-methylnaphthalen-2-yl)-2-(trityloxy)ethoxy)-2-methylpropan-1-ol

Participants

Reaction Steps

A solution of (S)-ethyl 2-(1-(1-chloro-3-methylnaphthalen-2-yl)-2-(trityloxy)ethoxy)-2-methylpropanoate (1.58 g, 2.66 mmol) in diethyl ether (62 mL) was treated with DIBAL-H (1.0 M in hexanes, 13.3 mL, 13.3 mmol) at 23° C. After 5 min, aq. Rochelle's salt (excess) was added dropwise over 5 min until bubbling ceased. The quenched reaction was agitated manually for 1 min to ensure full quenching. The system transitioned from a slurry to a gel. 50% w/v aw KOH (10 mL) was added, followed by H2O (40 mL), and the reaction was manually agitated until magnetic stirring was achievable (the reaction transitioned from a gel to a biphasic solution). After 15 min of stirring the reaction was extracted with diethyl ether (3×30 mL). Combined organic layers were dried quickly over MgSO4 for 1 min and promptly filtered and concentrated. The residue was treated with benzene and purified by flash column chromatography (silica gel, 0 to 100% ethyl acetate/hexanes) to give (S)-2-(1-(1-chloro-3-methylnaphthalen-2-yl)-2-(trityloxy)ethoxy)-2-methylpropan-1-ol. 1H NMR (400 MHz, CDCl3) δ 8.23 (d, J=8.2 Hz, 1H), 7.67 (d, J=7.8 Hz, 1H), 7.52-7.38 (m, 9H), 7.31-7.18 (m, 9H), 5.87 (dd, J=9.5, 3.9 Hz, 1H), 3.76 (d, AB-spin system, J=11.8 Hz, 1H), 3.60 (dd, J=9.6, 9.6 Hz, 1H), 3.32 (d, AB-spin system, J=11.8 Hz, 1H), 3.26 (dd, J=9.8, 3.9 Hz, 1H), 2.49 (s, 3H), 1.16 (s, 3H), 1.02 (s, 3H).

Provenance & Evidence