Cyclohexene oxide → HCID 18800751, compound

Temperature

0 °C

To a stirring THF solution of the Grignard reagent (formed from 2-(bromomethyl)tetrahydro-2H-pyran, 16a and powdered magnesium, 20 milligram-atoms) and cooled to -30° C., CuI is added as a bolus. After approx. 10 min., a solution of cyclohexene oxide (10 mmol) is added slowly, maintaining the reaction temperature below -25° C. until the addition is complete. The mixture is then stirred at 0° C. for 2 hours and checked by TLC and/or GC. The reaction is quenched by pouring into concentrated NH4Cl solution (if starting material remains, the reaction may be warmed to r.t. and followed by TLC or GC until no additional starting material is observed). Also, the addition of some concentrated NH4OH solution combined with vigorous stirring may be used to remove suspended CuI from the mixture. This mixture is then extracted with 2 portions of ether or 1:1 EA-hexane. The combined extracts are then washed with brine and dried (MgSO4). The product may be sufficiently pure at this point for use in the next reaction. Otherwise, it may be purified by distillation or flash chromatography.

1. temperaturemaintaining the reaction temperature below -25° C.
2. additionuntil the addition
3. customThe reaction is quenched
4. additionby pouring into concentrated NH4Cl solution (
5. customthe reaction
6. temperaturemay be warmed to r.t.
7. stirringwith vigorous stirring may
8. customto remove
9. extractionThis mixture is then extracted with 2 portions of ether or 1:1 EA-hexane
10. washThe combined extracts are then washed with brine
11. dry with materialdried (MgSO4)
12. customThe product may be sufficiently pure at this point for use in the next reaction
13. distillationOtherwise, it may be purified by distillation or flash chromatography

ORD record

ord-bf2444f911774b2eb96038e419370d1e

Source dataset

uspto-grants-2000_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06011028