Ethanol → HCID 11451301, compound

2.5 g of the product of step 8, 10% Pd/Al2O3 0.4 g and 50 ml of ethanol were combined in a 2-neck 100 ml round bottom flask. The reaction was hydrogenated at low pressure using standard conditions for 3 hours. The reaction was filtered through Celite to remove the catalyst, rinsed through with ethanol (100 ml). The filtrate was concentrated to ˜15 ml before being poured into chilled, stirred water (300 mL). A pale orange precipitate formed which then formed a brown oil. The mixture was then extracted with diethyl ether, the combined organic layers washed with water (3×100 ml), brine (1×100 ml), dried over anhydrous magnesium sulphate and filtered. The solvent was removed in vacuo to give red/brown oil. The product was recrystallised from diethyl ether (˜15 ml), to give brown solid which was rinsed with chilled diethyl ether to give off-white crystals. 4 crops of (IV), ˜1 g. The 1H NMR spectrum and numbering scheme being shown below.

1. customfor 3 hours
2. filtrationThe reaction was filtered through Celite
3. customto remove the catalyst
4. washrinsed through with ethanol (100 ml)
5. concentrationThe filtrate was concentrated to ˜15 ml
6. additionbefore being poured
7. temperatureinto chilled
8. customA pale orange precipitate formed which
9. customthen formed a brown oil
10. extractionThe mixture was then extracted with diethyl ether
11. washthe combined organic layers washed with water (3×100 ml), brine (1×100 ml)
12. dry with materialdried over anhydrous magnesium sulphate
13. filtrationfiltered
14. customThe solvent was removed in vacuo
15. customto give red/brown oil
16. customThe product was recrystallised from diethyl ether (˜15 ml)
17. customto give brown solid which
18. washwas rinsed with chilled diethyl ether
19. customto give off-white crystals

ORD record

ord-e7f5cebd2d534ca4ad84e17f58f8fe2c

Source dataset

uspto-grants-2009_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07601855B2