1,3-Dithiane → HCID 57859835, compound

Temperature

-78 °C

A solution of 1,3-dithiane (15.12 g, 126.0 mmol) in dry THF (150 mL) was treated at 0° C. with BuLi (53.0 mL of a 2.5 M solution, 132.5 mmol, 1.05 eqiuv) for 1.5 h. The reaction mixture was cooled to −78° C., and 2-bromoethyl methyl ether was added (11.3 mL, 16.7 g, 120.2 mmol). The reaction mixture was allowed to warm overnight to room temperature. The reaction was quenched by addition of saturated aqueous NH Cl. The mixture was extracted with Et2O. The combined organic extracts were washed with water. The mixture was dried over Na2SO4. The mixture was filtered. The filtrate was concentrated at reduced pressure. The residue was chromatographed [silica, ethyl acetate/hexanes (1:19)] affording a viscous, colorless liquid (21.53 g, 96%): 1H NMR δ 1.84-1.93 (m, 1H), 1.96-2.03 (m, 2H), 2.07-2.15 (m, 1H), 2.78-2.93 (m, 4H), 3.34 (s, 3H), 3.51-3.55 (m, 4H), 4.19 (t, J=6.9 Hz, 1H); 13C NMR δ 26.16, 30.40, 35.58, 44.16, 58.84, 68.92; EI-MS: 178 (M+), 146, 133, 119/121, 71/73, 45.

1. temperatureto warm overnight to room temperature
2. customThe reaction was quenched by addition of saturated aqueous NH Cl
3. extractionThe mixture was extracted with Et2O
4. washThe combined organic extracts were washed with water
5. dry with materialThe mixture was dried over Na2SO4
6. filtrationThe mixture was filtered
7. concentrationThe filtrate was concentrated at reduced pressure
8. customThe residue was chromatographed [silica, ethyl acetate/hexanes (1:19)]

ORD record

ord-69bad399122241d2a9e60df5004f1d46

Source dataset

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08207329B2