Dichloromethane → HCID 86705754, Verbindung

4-[6-chloro-5-(trifluoromethyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,3-benzodiazol-2-yl]butan-1-ol (1.00 g, 2.36 mmol) was dissolved in DCM (30 ml) and Dess-Martin reagent (1.10 g, 2.60 mmol) was added at r.t. The reaction was left for 4 hrs. The reaction was quenched by the addition of 1M Na2S2O3 solution (10 ml), sat. NaHCO3 solution (40 ml) and DCM (80 ml). The organic layer was separated and the aqueous layer was extracted with DCM (3×80 ml). The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo to give the crude product. The product was purified by silica flash column chromatography eluting with EtOAc:heptanes (1:1) as a light orange oil (0.53 g, 38%): MS (ESI+) for C18H24ClF3N2O2Si m/z 422.05 [M+H]+; LC purity 72% (ret. time, 1.81 min); 1H NMR (250 MHz, CHLOROFORM-d) δ ppm −0.21-0.21 (9H, m), 0.77-1.01 (2H, m), 2.17-2.36 (2H, m), 2.64-2.86 (2H, m), 3.02 (2H, td, J=7.39, 3.20 Hz), 3.35-3.74 (2H, m), 5.39-5.60 (2H, m), 7.34-8.18 (2H, m), 9.82 (1H, s).

1. customThe reaction was quenched by the addition of 1M Na2S2O3 solution (10 ml), sat. NaHCO3 solution (40 ml) and DCM (80 ml)
2. customThe organic layer was separated
3. extractionthe aqueous layer was extracted with DCM (3×80 ml)
4. dry with materialThe combined organic layers were dried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated in vacuo

ORD-Eintrag

ord-841bb0245a70470a98a20d85938773f5

Quelldatensatz

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09394310B2