2-Methyl-2-phenylpent-4-enal → 2-Methyl-2-phenylpent-4-en-1-ol

To a solution of 2-methyl-2-phenylpent-4-enal (4.6 g, 26.4 mmol) in 100 mL of THF was added of lithium aluminum hydride (LAH) (2.6 g, 68.51 mmol) in several portions. The mixture stirred for 3 hours at room temperature and was then refluxed for 2 hours. The reaction was monitored by TLC with ethyl acetate-hexanes (1:9) indicating a new more polar product. The reaction was cooled and the excess LAH was cautiously quenched with water dropwise. The mixture was then diluted with 1N aqueous HCl and extracted with 100 mL of hexanes and two 100 mL portions of ethyl acetate. The combined organic layers were washed with 50 mL of 1 N aqueous HCl, two 50 mL portions of brine, two 50 mL portions of saturated aqueous sodium bicarbonate, 50 mL of brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude material was chromatographed on silica gel using hexanes to load the sample and then eluting with 1% to 15% ethyl acetate-hexanes to afford 3.2 g (68.8) of 2-methyl-2-phenylpent-4-en-1-ol.

1. temperaturewas then refluxed for 2 hours
2. temperatureThe reaction was cooled
3. customthe excess LAH was cautiously quenched with water dropwise
4. additionThe mixture was then diluted with 1N aqueous HCl
5. extractionextracted with 100 mL of hexanes and two 100 mL portions of ethyl acetate
6. washThe combined organic layers were washed with 50 mL of 1 N aqueous HCl, two 50 mL portions of brine, two 50 mL portions of saturated aqueous sodium bicarbonate, 50 mL of brine
7. dry with materialdried over magnesium sulfate
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customThe crude material was chromatographed on silica gel
11. washeluting with 1% to 15% ethyl acetate-hexanes

ORD record

ord-594d5cc6fd724bfabe963cc15c3b76f7

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08741897B2