Réaction #717757

Équation de réaction

bis[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)oxalate

4-bromostyrene

magnesium

NH4Cl

→

oil

Rendement 47.1%

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-oxo-2-(4-vinylphenyl)acetate

Rendement 47.1%

Solvants

heptane ether

heptane ether

THF

THF

Conditions de réaction

Traitement

1. 1
   workup.WAITThe mixture was left
2. 2
   ExtractionExtraction with diethyl ether (2×)
3. 3
   Lavagewashing with water (3×)
4. 4
   Séchagedrying (Na2SO4)
5. 5
   Concentrationconcentrating
6. 6
   Autreafforded 6.42 g of the crude compound as an oil

Mode opératoire

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.

Source