Ethyl Acetate → 1-Naphthalen-1-yl-cyclopentanecarbaldehyde

To a solution of 1-naphthalen-1-yl-cyclopentanecarbonitrile (338) (10.5 g, 47.4 mmol) in dichloromethane (150 mL) was added dropwise diisobutylaluminium hydride (25% in toluene, 67.5 mL, 118.6 mmol) at −78° C. and stirred for 2 h at the same temperature (silica TLC, 5% ethyl acetate in hexane; Rf=0.6). The reaction mixture was quenched with a saturated aqueous solution of potassium sodium tarterate (35 mL) and stirred for 17 h at room temperature. The reaction mixture was filtered and the residue was washed with dichloromethane. The organic phase was separated and the aqueous part was back extracted with dichloromethane (100 mL). The combined organic part was dried, filtered and concentrated in vacuo to get a crude mass which was purified by CombiFlash using gradient eluent mixture of ethyl acetate and hexane to obtain pure 1-naphthalen-1-yl-cyclopentanecarbaldehyde (339) (10.4 g, 98%) as a colorless sticky liquid.

1. customThe reaction mixture was quenched with a saturated aqueous solution of potassium sodium tarterate (35 mL)
2. filtrationThe reaction mixture was filtered
3. washthe residue was washed with dichloromethane
4. customThe organic phase was separated
5. extractionthe aqueous part was back extracted with dichloromethane (100 mL)
6. customThe combined organic part was dried
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customto get a crude mass which
10. customwas purified by CombiFlash
11. additiongradient eluent mixture of ethyl acetate and hexane

ORD record

ord-2396c6eb2d90434092b7afcd2d5a68c5

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09045486B2