Sodium hydride → HCID 86607686, compound

To a solution of 7-Cyclopropyl-hept-5-ene-1,2-diol (1.45 g, 9.28 mmol) in THF (30 mL) was added 60% sodium hydride (1.1 g, 27.84 mmol) at 0° C. The mixture was slowly warmed to room temperature and stirred for 1 h. TrisIm (3.41 g, 10.2 mmol) was added in one portion at 0° C. followed stirring at room temperature for 1.5 h. The mixture was quenched with water and extracted with Et2O. The organics were washed with brine, dried over MgSO4, filtered, and concentrated. Purification by silica gel chromatography (7% EtOAc in hexanes gradient to 14% EtOAc in hexanes) gave 2-(4-Cyclopropyl-but-2-enyl)-oxirane as a clear oil; 1H NMR (400 MHz, CDCl3): δ 5.54–5.48 (m, 1H), 5.44–5.37 (m, 1H), 2.94–2.91 (m, 1H), 2.75 (dd, 1H, J1=4.9 Hz, J2=4.1 Hz), 2.48 (dd, 1H, J1=5.0 Hz, J2=2.7 Hz), 2.19 (q, 2H, J=7.3 Hz), 1.98 (t, 2H, J=7.0 Hz), 1.62–1.56 (m, 2H), 0.75–0.66 (m, 1H), 0.44–0.39 (m, 2H), 0.09–0.05(m, 2H).

1. additionTrisIm (3.41 g, 10.2 mmol) was added in one portion at 0° C.
2. stirringfollowed stirring at room temperature for 1.5 h
3. customThe mixture was quenched with water
4. extractionextracted with Et2O
5. washThe organics were washed with brine
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated
9. customPurification by silica gel chromatography (7% EtOAc in hexanes gradient to 14% EtOAc in hexanes)

ORD record

ord-c7e763e7c9814d9a9b402312eff92c42

Source dataset

uspto-grants-2007_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07241792B2