Hexane → Trans-4-bromocinnamaldehyde

To the product of Example 7.1B (8.35 g, 39.2 mmol) dissolved in dichloromethane (151 mL) was added pyridinium dichromate (22.11 g, 58.8 mmol), and the resultant mixture was stirred for 16 hours at room temperature. A solution of hexane was added, and the resultant mixture filtered through diatomaceous earth, and then concentrated. Water was added to the residue, and the mixture was extracted with ethyl acetate. The organic layers were combined, dried and then concentrated. The residue was purified by chromatography (silica gel, hexanes in ethyl acetate) which afforded 5.5 g, (67%) of the title compound. 1H NMR (400 MHz, CDCl3) δ ppm 9.62 (d, J=7.6 Hz, 1H), 7.57 (d, J=8.5 Hz, 2H), 7.42 (m, 3H), 6.70 (dd, J=15.9, 7.6 Hz, 1H).

1. filtrationthe resultant mixture filtered through diatomaceous earth
2. concentrationconcentrated
3. additionWater was added to the residue
4. extractionthe mixture was extracted with ethyl acetate
5. customdried
6. concentrationconcentrated
7. customThe residue was purified by chromatography (silica gel, hexanes in ethyl acetate) which

ORD-Eintrag

ord-cd9a7b181d004c289fe2a80cadd07e17

Quelldatensatz

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08921514B2