Iodine chloride → HCID 22724558, compound

A mixture of 4-(4-nitrobenzylidene)tetrahydro-2H-pyran (2.0 g) and PtO2 (0.2 g) is hydrogenated at 40 p.s.i. H2 for 3.5 h. The mixture is filtered through celite and the filtrate condensed. The crude residue is dissolved in a mixture of 40 mL CHCl3 and 4 mL MeOH. To this is added sodium acetate (2.24 g), followed by the dropwise addition of a solution of ICl (0.69 mL) in MeOH (10 mL). The reaction is stirred at room temperature for 1 h then quenched by pouring into an iced saturated solution of aqueous sodium bisulfite (200 mL). The mixture is stirred for 30 minutes then concentrated until all of the organics are gone. The aqueous solution is extracted with CH2Cl2 (3×). The combined organic layers are washed with brine, dried and condensed. The crude product is chromatographed (Biotage flash 40M, eluent CH2Cl2) to yield 1.0 g (34%) of the desired product as a yellow oil.

1. filtrationThe mixture is filtered through celite
2. customthe filtrate condensed
3. customthen quenched
4. additionby pouring into an iced saturated solution of aqueous sodium bisulfite (200 mL)
5. stirringThe mixture is stirred for 30 minutes
6. concentrationthen concentrated until all of the
7. extractionThe aqueous solution is extracted with CH2Cl2 (3×)
8. washThe combined organic layers are washed with brine
9. customdried
10. customcondensed
11. customThe crude product is chromatographed (Biotage flash 40M, eluent CH2Cl2)

ORD record

ord-7a391f57ea3d4be5a13c8fe72b208ad4

Source dataset

uspto-grants-2004_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06727248B2