4-Bromostyrene → HCID 90409758, compound

Participants

Reaction Steps

A Grignard reagent prepared from 4-bromostyrene (2.75 g, 15.0 mmol) and magnesium (0.39 g, 16.0 mmol) in THF (20 mL) was added dropwise (during a period of 20 min) to a stirred solution of bis[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)oxalate (5.00 g, 13.7 mmol) in THF (15 mL) at −60° C. The mixture was left warming to room temperature and poured into a mixture of ice (200 g) and a saturated solution of NH4Cl (10 mL). Extraction with diethyl ether (2×), washing with water (3×), drying (Na2SO4) and concentrating afforded 6.42 g of the crude compound as an oil. Repetitive column chromatography (SiO2, heptane/ether 7:3 and heptane/ether 95:5) gave 2.03 g (47%) of an oil.

Provenance & Evidence