Hydrochloric Acid → Furan, 2-(3-iodopropyl)-

To a solution of 3-furan-2-yl-propan-1-ol (6.3 g, 50 mmol) in pyridine (40 mL) at −15° C. was added p-toluenesulfonyl chloride (11.4 g, 60 mmol) in portions and the reaction was stirred for 3 h. Water (10×0.5 mL) was added and the mixture was poured into a mixture of concentrated HCl (65 mL) and ice (200 gm). The product was extracted into Et2O and the organic solution was dried over MgSO4, filtered, and concentrated to provide a yellow oil. The oil was added to a mixture of NaI (9 g, 60 mmol) in acetone (70 mL) and the reaction was stirred for 15 h. The insolubles were removed by filtration and the filtrate was concentrated in vacuo. Purification by flash chromatography (hexanes) provided the title compound (7.2 g). 1H NMR (400 MHz, CDCl3) δ 7.30 (m, 1H), 6.28 (m, 1H), 6.04 (m, 1H), 3.19 (t, 2H), 2.75 (t, 2H), 2.14 (m, 2H).

1. extractionThe product was extracted into Et2O
2. dry with materialthe organic solution was dried over MgSO4
3. filtrationfiltered
4. concentrationconcentrated
5. customto provide a yellow oil
6. stirringthe reaction was stirred for 15 h
7. customThe insolubles were removed by filtration
8. concentrationthe filtrate was concentrated in vacuo
9. customPurification by flash chromatography (hexanes)

ORD record

ord-aacc5648efaf4a70861b7b725f7df9d6

Source dataset

uspto-grants-2002_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06492412B2