HCID 67313169, compound → HCID 57699580, compound

A solution of 2,2-dimethyl-4-{3-[(phenylmethyl)oxy]propylidene}tetrahydro-2H-pyran (5.98 g, 22.97 mmol) in ethyl acetate (70 ml) was hydrogenated over 10% palladium on activated carbon (0.733 g, 0.689 mmol) at atmospheric pressure and room temperature. After 16 hours, the mixture was filtered under vacuum through Celite, washed through with EtOAc (2×50 mL) and the filtrate was evaporated to dryness to give a yellowish mobile oil. 1H NMR showed that most of the benzyl group had been hydrogenated but the double bond was still present. The residue was dissolved in ethyl acetate (70 ml) and was hydrogenated over 10% palladium on activated carbon (1.1 g) at atmospheric pressure and room temperature. After 16 hours, the mixture was filtered under vacuum through Celite, washed through with EtOAc (2×50 mL) and the filtrate was evaporated to dryness to give a yellowish mobile oil. The residue was purified by chromatography on silica (100 g) using a cyclohexane:ethyl acetate 0->50% gradient over 40 mins on a Flashmaster II. The desired fractions (analysed with a permanganate dip) were combined and concentrated under vacuum to give the title compound as a pale yellow oil (2.17 g).

1. filtrationthe mixture was filtered under vacuum through Celite
2. washwashed through with EtOAc (2×50 mL)
3. customthe filtrate was evaporated to dryness
4. customto give a yellowish mobile oil
5. waitAfter 16 hours
6. filtrationthe mixture was filtered under vacuum through Celite
7. washwashed through with EtOAc (2×50 mL)
8. customthe filtrate was evaporated to dryness
9. customto give a yellowish mobile oil
10. customThe residue was purified by chromatography on silica (100 g)
11. waitethyl acetate 0->50% gradient over 40 mins on a Flashmaster II
12. concentrationconcentrated under vacuum

ORD record

ord-6c455475484549a9bb6115566fda850e

Source dataset

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07977344B2