Sodium Iodide → HCID 15599359, compound

A flame dried, N2 purged 1-liter, 3-neck round bottom flask equipped with an internal thermometer and mechanical stirrer was charged with 5-benzyloxy-6-(methanesulfonyloxymethyl)-2,3-dihydrobenzofuran (30.60 g, 0.10 moles) and anhydrous acetone (250 ml). The resultant solution was cooled to 0° C. and with efficient stirring sodium iodide (59.90 g, 0.40 moles) in acetone (150 ml) was added in one portion. The reaction mixture was stirred at room temperature for 72 hours and then suction filtered through a bed of celite. The filtrate was concentrated in vacuo to afford the crude product. This was dissolved in ethyl ether (400 ml) and water (200 ml), the layers partitioned, and separated. The organic phase was washed with saturated NaHS03 solution (2×200 ml) and water (1×200 ml), dried over MgSO4, suction filtered, and the filtrate concentrated in vacuo to yield 5-benzyloxy-6-iodomethyl-2,3-dihydrobenzofuran as a yellow solid (33.0 g, 98%).

1. customA flame dried
2. customN2 purged 1-liter, 3-neck round bottom flask
3. customequipped with an internal thermometer and mechanical stirrer
4. additionwas added in one portion
5. filtrationsuction filtered through a bed of celite
6. concentrationThe filtrate was concentrated in vacuo
7. customto afford the crude product
8. customwater (200 ml), the layers partitioned
9. customseparated
10. washThe organic phase was washed with saturated NaHS03 solution (2×200 ml) and water (1×200 ml)
11. dry with materialdried over MgSO4, suction
12. filtrationfiltered
13. concentrationthe filtrate concentrated in vacuo

ORD record

ord-adfea92aadc04735ac171a3b9ee37262

Source dataset

uspto-grants-1988_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04775679