Imidazole → 17-Acetoxy-heptadecyl iodide

Temperature

0 °C

17-Acetoxy-heptadecanol (4.4 g, 13.99 mmol), Ph3P (4.4 g, 16.78 mmol) and imidazole (1.57 g, 23.08 mmol) were dissolved in the mixture of CH2Cl2 (40 ml) and benzene (20 ml). The mixture was cooled to 0° C. and solid I2 (4.26 g, 16.78 mmol) was added in one portion. The mixture was stirred at 0° C. for 15 min and at room temperature for 30 min. The reaction was quenched by the addition of EtOH (1.5 ml), stirred for 10 min at room temperature, diluted with hexane-EtOAc (1:1) mixture and washed with aqueous NaHCO3—Na2S2O3 solution. The organic extract was dried Na2SO4 and evaporated. Residue was stirred with hexane (300 ml) for 20 min and the suspension was filtered to remove Ph3PO. The filtrate was evaporated and the residue was chromatographed on silica gel in hexane-EtOAc (98:2) to give 17-acetoxy-heptadecyl iodide (5.89 g, 99%).

1. customThe reaction was quenched by the addition of EtOH (1.5 ml)
2. stirringstirred for 10 min at room temperature
3. additiondiluted with hexane-EtOAc (1:1) mixture
4. washwashed with aqueous NaHCO3—Na2S2O3 solution
5. extractionThe organic extract
6. customevaporated
7. stirringResidue was stirred with hexane (300 ml) for 20 min
8. filtrationthe suspension was filtered
9. customto remove Ph3PO
10. customThe filtrate was evaporated
11. customthe residue was chromatographed on silica gel in hexane-EtOAc (98:2)

ORD record

ord-fee124341e2549b0aad8119c57f1a20c

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07893286B2