反应详情

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).

1. customuntil bubbling
2. customThe quenched reaction
3. additionwas added
4. stirringthe reaction was manually agitated
5. stirringuntil magnetic stirring
6. stirringAfter 15 min of stirring the reaction
7. extractionwas extracted with diethyl ether (3×30 mL)
8. dry with materialCombined organic layers were dried quickly over MgSO4 for 1 min
9. filtrationpromptly filtered
10. concentrationconcentrated
11. additionThe residue was treated with benzene
12. custompurified by flash column chromatography (silica gel, 0 to 100% ethyl acetate/hexanes)