Triethylamine → HCID 59479413, compound

Participants

Reaction Steps

To 76B (ca 31 mmol) in CH2Cl2 (150 mL) at −15° C. was added Et3N (5.94 mL, 43 mmol) followed by TiCl4 (1.0 M in CH2Cl2, 37.2 mL, 37.2 mmol). The mixture was stirred from −15° C. to rt over 3.0 h before it was quenched with sat. K2CO3 (200 mL) at 0° C. and stirred at rt for 1.0 h. CH2Cl2 was removed under vacuo and EtOAc was added to the crude (for better filtration). The mixture was filtered through a pad of wet Celite®, extracted with EtOAc (3×100 mL). The organic layer was washed with water, dried over Na2SO4. The cude was purified by silica gel flash column chromatography using gradient CH2Cl2 in hexanes to give 76C (3.77 g, 56% yield) and retrieved 76A (2.8 g). LC-MS indicated a mixture of cis and trans isomer in ca. 1:1 ratio. LC-MS 337 (M+H).

Provenance & Evidence