Hydrochloric Acid → HCID 10858216, Verbindung

Temperatur

-20 °C

To a solution of (R)-2-methylbutane-1,4-diol (30 g, 0.29 mol) in dichloromethane (600 mL) was added triethylamine (100 mL, 0.72 mol). The solution was cooled to −20° C., and methanesulfonyl chloride (49 mL, 0.63 mol) was added dropwise over 30 min with vigorous stirring. The resulting mixture was stirred for additional 1 h while the temperature was maintained between −20 and −15° C. The mixture was allowed to warm to 0° C. and then poured into cold 1N HCl solution (100 mL). The organic layer was separated, and aqueous phase was extracted with dichloromethane (100 mL). The combined organic extracts were washed with sat'd NaHCO3 solution, brine, dried over MgSO4, filtered and concentrated in vacuo. The resulting product (75.9 g, quant) was used directly for the next step. 1H NMR (400 MHz, CDCl3): δ 4.41-4.24 (m, 2H), 4.12 (dq, 2H), 3.02 (d, 6H), 2.13 (td, 1H), 1.95 (td, 1H), 1.80-1.65 (m, 1H), 1.07 (d, 3H).

1. temperaturewas maintained between −20 and −15° C
2. temperatureto warm to 0° C.
3. customThe organic layer was separated
4. extractionaqueous phase was extracted with dichloromethane (100 mL)
5. washThe combined organic extracts were washed with sat'd NaHCO3 solution, brine
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo

ORD-Eintrag

ord-942e9a578566417d8568243c5e7b42ae

Quelldatensatz

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09399646B2