Aluminium lithium hydride → 2-(2-(2-Allyloxy-ethoxy)-ethoxy)-ethanol

To a stirred solution of ester (14) (4.60 g, 21.1 mmol, 1.0 equiv.) in THF (60 mL) was carefully added one portion of LAH (0.50 g, 12.5 mmol, 0.5 equiv.) at 0° C. After 30 min, another portion of LAH was carefully added and the reaction was stirred for an additional 30 min. The reaction was then carefully quenched with a Na2SO4-saturated aqueous solution. The resulting white aluminum salts were then filtered off over a short plug of Celite (EtOAc washings) and the filtrate was finally evaporated under reduced pressure to afford pure alcohol (15) (no purification required) as a pale yellow oil (3.89 g, 97%). Spectroscopic data were consistent with those reported in the literature:26a 1H NMR (400 MHz, CDCl3) δ 5.93 (ddt, J=17.2, 10.3, 5.7 Hz, 1H), 5.28 (dq, J=17.2, 1.5 Hz, 1H), 5.19 (dq, J=10.3, 1.5 Hz, 1H), 4.04 (dt, J=5.7, 1.5 Hz, 2H), 3.78-3.58 (m, 12H); 13C NMR (75 MHz, CDCl3) δ 134.8, 117.3, 72.7, 72.4, 70.8, 70.7, 70.5, 69.5, 61.8.

1. customThe reaction was then carefully quenched with a Na2SO4-saturated aqueous solution
2. filtrationThe resulting white aluminum salts were then filtered off over a short plug of Celite (EtOAc washings)
3. customthe filtrate was finally evaporated under reduced pressure

ORD record

ord-7e0dc18440924d72b11a52c3b05cc1fe

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08491958B2