Hexachloroethane → HCID 66696678, compound

Temperature

-78 °C

A solution of Example 33A (0.94 g, 4.8 mmol) in THF (20 mL) was cooled to −78° C., then treated slowly with LiHMDS (1M in THF, 6.3 mL, 6.3 mmol). The reaction was stirred at −78° C. for 20 min and then treated all at once with solid hexachloroethane (2.31 g, 9.75 mmol). The flask was removed from the cold bath, and the reaction mixture was allowed to stir overnight at room temperature. After this time, it was poured into water and extracted with Et2O. The combined Et2O extracts were concentrated in vacuo, and the residue was chromatographed on silica gel (Analogix® SF25-60 column; 100% hexane for 10 minutes, then 0% to 15% EtOAc/hexanes over 10 minutes) to afford 0.673 g (61%) of the title compound as a bright yellow oil. 1H NMR (300 MHz, DMSO-d6) δ 7.17 (d, J=3.6, 1H), 6.93 (dt, J=3.7, 1.0 1H), 2.86 (qd, J=7.6, 1.0 2H), 2.27 (s, 3H), 1.26 (t, J=7.5, 3H). MS (DCI+) m/z 228 (M+H).

1. customThe flask was removed from the cold bath
2. stirringto stir overnight at room temperature
3. additionAfter this time, it was poured into water
4. extractionextracted with Et2O
5. concentrationThe combined Et2O extracts were concentrated in vacuo
6. customthe residue was chromatographed on silica gel (Analogix® SF25-60 column
7. wait100% hexane for 10 minutes

ORD record

ord-69a98f1416894a138f3a84942bb45ccb

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07998993B2