Water → HCID 86596724, compound

0.485 mol (75.8 g) of the (2E)-5-methyl-hex-2-ene carboxylic acid ethyl ester produced according to 2.1. were dissolved under a nitrogen atmosphere in THF (abs.). 0.73 mol (39.1 ml) of nitromethane and 0.49 mol (485 ml) of a 1 molar tetrabutylammonium fluoride solution in THF were added, wherein an orange solution arose. The mixture was refluxed for 20 hours. After cooling, the mixture was combined with 280 ml of water and extracted four times with diethyl ether. The organic phase was extracted three times with 10% aqueous potassium hydrogensulfate solution and washed to neutrality with water. The organic phase was dried with magnesium sulfate and evaporated in a rotary evaporator. An orange liquid was obtained. The crude yield amounted to 95.2 g (90% of theoretical).

1. temperatureThe mixture was refluxed for 20 hours
2. temperatureAfter cooling
3. extractionextracted four times with diethyl ether
4. extractionThe organic phase was extracted three times with 10% aqueous potassium hydrogensulfate solution
5. washwashed
6. dry with materialThe organic phase was dried with magnesium sulfate
7. customevaporated in a rotary evaporator
8. customAn orange liquid was obtained
9. customThe crude yield

ORD record

ord-caa93c1016824689ba03f386eb1afe8f

Source dataset

uspto-grants-2006_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07141695B2