2-Iodophenol → HCID 21833837, compound

A stirred solution of 2-iodophenol (8.8 g, 0.040 mole), triphenylphosphine (10.5 g, 0.040 mole) and 2-(4-pyridyl)ethanol (D65, 5.5 g, 0.045 mole) in THF (200 ml) at 0° C. under argon was treated with a solution of diethyl azodicarboxylate (6.3 ml, 0.040 mole) in THF (30 ml). The solution was allowed to warm to room temp. and stirred for 4 h, then concentrated in vacuo and the residue treated with 10% Na2CO3 solution (80 ml) and extracted with ethyl acetate (2×80 ml). The combined organic was extracted with 1M HCl acid (150 ml), then the acid extract basified by addition of potassium carbonate and extracted with ethyl acetate (2×100 ml). The combined extract was dried (Na2SO4) and concentrated in vacuo to leave a brown oil, which was chromatographed on silica gel eluting with 0 to 15% ethyl acetate/ether to afford the title compound as a colourless oil (9.3 g, 72%).

1. temperatureto warm to room temp.
2. concentrationconcentrated in vacuo
3. additionthe residue treated with 10% Na2CO3 solution (80 ml)
4. extractionextracted with ethyl acetate (2×80 ml)
5. extractionThe combined organic was extracted with 1M HCl acid (150 ml)
6. extractionthe acid extract
7. additionbasified by addition of potassium carbonate
8. extractionextracted with ethyl acetate (2×100 ml)
9. extractionThe combined extract
10. dry with materialwas dried (Na2SO4)
11. concentrationconcentrated in vacuo
12. customto leave a brown oil, which
13. customwas chromatographed on silica gel eluting with 0 to 15% ethyl acetate/ether

ORD record

ord-920db7b970ec4174bf985110a22e3f49

Source dataset

uspto-grants-1999_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05972951