Hydrochloric Acid → 1-(2-Methyl-1H-inden-4-yl)naphthalene

1.3 g (33 mmol) of sodium borohydride were added at 0° C. to a solution of 12 g (44 mmol) of (16) in 100 ml of THF/methanol 2:1 and the mixture was stirred for 18 hours at room temperature. The reaction mixture was poured onto 100 g of ice, concentrated hydrochloric acid was added until the pH was 1 and the mixture was extracted a number of times with diethyl ether. The combined organic phases were washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated aqueous sodium chloride solution and dried over magnesium sulfate. The crude product was taken up in 200 ml of toluene, admixed with 0.5 g of p-toluenesulfonic acid and refluxed for 2 hours on a water separator. The reaction mixture was washed 3 times with 509 ml each time of saturated sodium hydrogen carbonate solution and the solvent was removed under reduced pressure. The solid residue was washed with a little pentane and dried under reduced pressure. This gave 10.3 g of (37) in the form of colorless crystals.

1. additionwas added until the pH was 1
2. extractionthe mixture was extracted a number of times with diethyl ether
3. washThe combined organic phases were washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated aqueous sodium chloride solution
4. dry with materialdried over magnesium sulfate
5. temperaturerefluxed for 2 hours on a water separator
6. washThe reaction mixture was washed 3 times with 509 ml each time of saturated sodium hydrogen carbonate solution
7. customthe solvent was removed under reduced pressure
8. washThe solid residue was washed with a little pentane
9. customdried under reduced pressure

ORD record

ord-54bf7e1f7eb44910b6ff0f696f5f7b3f

Source dataset

uspto-grants-2005_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06963017B2