Cerium(III) chloride → HCID 178459058, compound

Participants

Reaction Steps

To the suspension of cerium(III) chloride (86 mg, 0.35 mmol) in THF (3 mL) was added the product from Example 77 (100 mg, 0.23 mmol) in THF (0.5 mL). The mixture was stirred at rt for 1 hr. The above mixture was cooled to −40° C. and methylmagnesium bromide (41.6 mg, 0.348 mmol) was added dropwise. The reaction was stirred for 40 min at −40° C., quenched with saturated aqueous NH4Cl and extracted with CH2Cl2 (2×). The combined organic layers were dried over MgSO4, filtered and concentrated. The residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 0-50% Hexane in ethyl acetate) to afford 57 mg (55%) of the title compound. 1H NMR (500 MHz, CDCl3) δ ppm 1.23 (s, 6 H) 1.57-1.61 (m, 2 H) 1.68 (s, 9 H) 1.74 (s, 1 H) 1.81-1.89 (m, 2 H) 2.88 (t, J=7.63 Hz, 2 H) 7.30 (t, J=7.93 Hz, 1 H) 7.69 (t, J=6.41 Hz, 1 H) 8.01-8.04 (m, 1 H) 8.39 (td, J=7.93, 1.53 Hz, 1 H); MS (DCI/NH4+) m/z 447 (M+H)+.

Provenance & Evidence