Aluminium lithium hydride → HCID 69494660, compound

To a solution of (2-ethoxy-5-methoxycarbonylmethyl-[1,3]dioxolan-4-yl)-acetic acid methyl ester (Ex-14B, 11.0 g, 42 mmol) in tetrahydrofuran (75 mL) at 0° C. was added a solution of LAH in tetrahydrofuran (1 M, 63 mL, 63 mmol) dropwise over a 1 h period. The reaction mixture was allowed to warm to rt and stir for 2 h at which time the solution was then cooled back down to 0° C. and carefully quenched with sodium sulfate decahydrate. The mixture was concentrated under reduced pressure and the residue was diluted with equal portions of a saturated Rochelle salt solution and ethyl acetate (approx. 150 mL each) and the slurry was vigorously stirred overnight. The layers were then separated and the aqueous layer was extracted with ethyl acetate (4×100 mL), the organic extracts dried over sodium sulfate, filtered and concentrated under reduced pressure. Drying in vacuo gave 2-[2-ethoxy-5-(2-hydroxy-ethyl)-[1,3]dioxolan-4-yl]-ethanol (7.6 g, 88%) as a colored oil. This material was used without further purification. 1H-NMR (300 MHz, CDCl3) δ5.82(s, 1H), 4.11–4.17 (m, 1H,), 3.92–3.97 (m, 1H), 3.80–3.86 (m, 4H), 3.61 (q, 2H, J=7.0 Hz), 2.30 (brs, 1H), 2.22 (brs, 1H), 1.76–1.94 (m, 4H), 1.23 (t, 3H, J=7.0 Hz).

1. temperaturewas then cooled back down to 0° C.
2. customcarefully quenched with sodium sulfate decahydrate
3. concentrationThe mixture was concentrated under reduced pressure
4. additionthe residue was diluted with equal portions of a saturated Rochelle salt solution and ethyl acetate (approx. 150 mL each)
5. waitthe slurry was vigorously stirred overnight
6. customThe layers were then separated
7. extractionthe aqueous layer was extracted with ethyl acetate (4×100 mL)
8. dry with materialthe organic extracts dried over sodium sulfate
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure
11. customDrying in vacuo

ORD record

ord-b508c13ff4e3490ab215f0576dd08826

Source dataset

uspto-grants-2007_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07271274B2