Triethylamine → HCID 57966308, compound

To a mixture of 3-(methoxymethoxy)-4-methylbenzyl alcohol described in WO2004/022551 (9.80 g; 53.78 mmol), triethylamine (7.90 ml; 56.47 mmol) and anhydrous THF (50 ml) was added dropwise methanesulfonyl chloride (4.40 ml; 56.47 mmol) under ice-cooling. The mixture was stirred at the same temperature for 1.5 hours. The precipitate was collected and condensed under reduced pressure. Then, to the residue were added sodium cyanide (7.91 g; 0.161 mol) and anhydrous N,N-dimethylformamide (50 ml). The mixture was stirred at room temperature for 3 days. Water and ethyl acetate were added to the reaction solution. The organic layer was separated, washed with brine, dried over anhydrous sodium sulphate, and evaporated under reduced pressure. The residue was purified by column chromatograph on silica gel (hexane:ethyl acetate=3:1) to give [3-(methoxymethoxy)-4-methylphenyl]acetonitrile as blackish brown oil (7.87 g; 77%).

1. temperaturecooling
2. customThe precipitate was collected
3. customcondensed under reduced pressure
4. stirringThe mixture was stirred at room temperature for 3 days
5. customThe organic layer was separated
6. washwashed with brine
7. dry with materialdried over anhydrous sodium sulphate
8. customevaporated under reduced pressure
9. customThe residue was purified by column chromatograph on silica gel (hexane:ethyl acetate=3:1)

ORD record

ord-e8e62901dd14424abccdefc098df9b49

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08097610B2