Methyl iodide → HCID 86622399, compound

Temperature

7.5 °C

The title compound is prepared by the method described in Bull. Chem. Soc. Jpn. (2000), 73, 477f.: To a cooled solution of 3-ethoxy-1-propanol (24.4 g, 0.227 mol) in DMF (150 mL) is added NaH (60% dispersion in oil; 10.0 g, 0.250 mol) in portions over 1 hour, keeping the reaction temperature below 5° C. Stirring is continued for 5 hrs at room temperature, the mixture is cooled to 5 to 10° C. followed by dropwise addition of CS2 (27.5 mL, 0.454 mol). The mixture is gradually warmed to ambient temperature overnight and then cooled to <10° C. before adding iodomethane (17.9 mL, 0.284 mol). Stirring is continued for 18 hrs at room temperature, the mixture is then poured into ice-cold diluted aqueous HCl and extracted with diethyl ether. The combined organic layers are washed with brine, dried over MgSO4 and concentrated to give a yellow oil. Purification by flash chromatography on silica gel (hexane/AcOEt 20:1) gives the title compound as yellow liquid. TLC, Rf (hexane/AcOEt 3:1)=0.56. 1H-NMR (CDCl3): δ 1.23 (t, 3H), 2.11 (m, 2H), 2.60 (s, 3H), 3.52 (t, 2H), 3.58 (t, 2H), 4.79 (t, 2H) ppm.

1. customThe title compound is prepared by the method
2. customthe reaction temperature below 5° C
3. temperatureThe mixture is gradually warmed to ambient temperature overnight
4. temperaturecooled to <10° C.
5. stirringStirring
6. waitis continued for 18 hrs at room temperature
7. additionthe mixture is then poured into ice-cold diluted aqueous HCl
8. extractionextracted with diethyl ether
9. washThe combined organic layers are washed with brine
10. dry with materialdried over MgSO4
11. concentrationconcentrated
12. customto give a yellow oil
13. customPurification by flash chromatography on silica gel (hexane/AcOEt 20:1)

ORD record

ord-0e04b2c0b409439d805adef80e1c67b3

Source dataset

uspto-grants-2010_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07807709B2