2-Naphthalenecarboxaldehyde → HCID 13900156, compound

Temperature

-78 °C

To a stirred solution of acetonitrile (2.46 g, 60 mmol, 3.13 mL) in THF (300 mL) at -78° C. was added N-BuLi (37.5 mL, 60 mmol, 1.6M) dropwise over 30 minutes. The resulting solution was stirred at -78° C. for 15 minutes and then 2-naphthaldehyde (6.24 g, 40 mmol) in THF (50 mL) was added dropwise over 45 minutes. The resulting mixture was stirred for an additional 20 minutes at -78° C. and quenched at -78° C. by the addition of saturated NH4Cl (60 mL). The mixture was warmed to room temperature and the THF removed in vacuo to give a white solid. The residue was partitioned between CH2Cl2 (250 mL) and H2O (200 mL, the layers were separated and the aqueous phase extracted with CH2Cl2 (1×250 mL). The combined organic layers were washed with H2O (1×250 ML), dried (Na2SO4) and concentrated in vacuo to give the title compound as a tan solid (7.88 g, 100%) which was homogeneous by TLC and NMR. This material was used as such without purification.

1. stirringThe resulting mixture was stirred for an additional 20 minutes at -78° C.
2. customquenched at -78° C. by the addition of saturated NH4Cl (60 mL)
3. temperatureThe mixture was warmed to room temperature
4. customthe THF removed in vacuo
5. customto give a white solid
6. customThe residue was partitioned between CH2Cl2 (250 mL) and H2O (200 mL
7. customthe layers were separated
8. extractionthe aqueous phase extracted with CH2Cl2 (1×250 mL)
9. washThe combined organic layers were washed with H2O (1×250 ML)
10. dry with materialdried (Na2SO4)
11. concentrationconcentrated in vacuo

ORD record

ord-c55f3f2a068041b1b07b1d23d799b059

Source dataset

uspto-grants-1990_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04895861