Methyl iodide → HCID 58906458, Verbindung

Alcohol (35)-(69.3 g, 200 mmol) was dissolved in dimethyl formamide (500 ml). NaH (9.2 g 230 mmol), washed with pentane, was added in 5 portions over 30 min. After complete addition the mixture was stirred at ambient temperature for 45 min. Methyl iodide (14.8 ml, 240 mmol) was added over 1.5 min. The mixture was stirred for 1.5 h at ambient temperature. TLC analysis revealed ca. 80-90% conversion. Extra NaH, 0.8 g, 20 mmol) and methyl iodide (1.2 ml, 20 mmol) was added and the mixture was stirred for another 2 h at ambient temperature. The excess of NaH was destroyed with water (100 ml) and the mixture was further diluted with water (3.5 l). The mixture was extracted with ethyl acetate (2×1 l, 500 ml). The organic layer was washed with brine (1 l), dried over Na2SO4 and concentrated to dryness. The traces of dimethyl formamide were removed by evaporation in vacuo (0.4 mbar, 80° C.). The remaining mixture was purified over silica (eluent: heptane/ethyl acetate, 4/1 to 3/1 v/v). Yield: 55.2 g of amine (36) (80%) as light yellow oil.

1. additionwas added in 5 portions over 30 min
2. additionAfter complete addition the mixture
3. stirringThe mixture was stirred for 1.5 h at ambient temperature
4. stirringthe mixture was stirred for another 2 h at ambient temperature
5. customThe excess of NaH was destroyed with water (100 ml)
6. additionthe mixture was further diluted with water (3.5 l)
7. extractionThe mixture was extracted with ethyl acetate (2×1 l, 500 ml)
8. washThe organic layer was washed with brine (1 l)
9. dry with materialdried over Na2SO4
10. concentrationconcentrated to dryness
11. customThe traces of dimethyl formamide were removed by evaporation in vacuo (0.4 mbar, 80° C.)
12. customThe remaining mixture was purified over silica (eluent: heptane/ethyl acetate, 4/1 to 3/1 v/v)

ORD-Eintrag

ord-d390d50cd28a47c6b6b8814397bcf237

Quelldatensatz

uspto-grants-2007_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07241770B2