Methanol → HCID 6479255, compound

Under an atmosphere of nitrogen a 1M solution of DIBAL-H in toluene (82 ml, 82 mmol) was added dropwise at −70° C. over 20 min. to a stirred solution of (E)-3-quinolin-2-yl-acrylic acid ethyl ester (12.5 g, 55 mmol) in dry THF (400 ml) and the mixture stirred for 3 h. Methanol (100 ml) was added, and the mixture was concentrated in vacuo. The residue was dissolved in 1N HCl (500 mL) and ethyl acetate (100 mL). The aqueous phase was separated and added 1 N NaOH to pH 8. The product was extracted with dichloromethane. The combined organic phases were washed with water, dried (MgSO4), filtered and concentrated in vacuo. The residue was dissolved in ethyl acetate, treated with activated charcoal, filtered, and concentrated in vacuo yielding 5.6 g (56%) of (E)-3-quinolin-2-yl-prop-2-en-1-ol.

1. concentrationthe mixture was concentrated in vacuo
2. dissolutionThe residue was dissolved in 1N HCl (500 mL)
3. customThe aqueous phase was separated
4. additionadded 1 N NaOH to pH 8
5. extractionThe product was extracted with dichloromethane
6. washThe combined organic phases were washed with water
7. dry with materialdried (MgSO4)
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. dissolutionThe residue was dissolved in ethyl acetate
11. additiontreated with activated charcoal
12. filtrationfiltered
13. concentrationconcentrated in vacuo

ORD record

ord-0393d21d2515488d8137c5d80a0b048b

Source dataset

uspto-grants-2006_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07067530B2