1-Naphthaldehyde → HCID 10198689, compound

Temperature

-78 °C

To a −78° C. solution of 1-naphthaldehyde (13.0 mL, 96.1 mmol) and ethyl chloroacetate (10.3 mL, 96.1 mmol) in tetrahydrofuran (900 mL) was added (1.0 M in tetrahydrofuran) sodium bis(trimethylsilyl)amide (96.1 ml, 96.1 mmol) dropwise. The reaction mixture was stirred at −78° C. for 30 minutes and then warmed to 0° C. The reaction was then quenched with water (200 mL). The reaction mixture was then diluted with ethyl acetate (800 mL). The organic reaction layer was then washed in succession with water and saturated sodium chloride, the organic layer was then dried over magnesium sulfate, filtered and concentrated under reduced pressure to yield a pale oil. The crude residue was chromatographed (silica gel with 5% ethyl acetate-95% hexane) to give 3-naphthalen-1-yl-oxirane-2-carboxylic acid ethyl ester as a clear oil. 1H NMR(300 MHz, DMSO) 8.12 (d, 1H), 7.95 (m, 2H), 7.51 (m, 4H), 4.77 (d, 1H), 4.24 (q, 2H), 3.72 (d, 1H), 1.27 (t, 3H). MS(APCI) m/z 241.1 (M−H). Anal. Calcd. for C15H14O3: C, 74.36; H, 5.82. Found: C, 74.47; H, 5.87.

1. temperaturewarmed to 0° C
2. customThe reaction was then quenched with water (200 mL)
3. additionThe reaction mixture was then diluted with ethyl acetate (800 mL)
4. washThe organic reaction layer was then washed in succession with water and saturated sodium chloride
5. dry with materialthe organic layer was then dried over magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customto yield a pale oil
9. customThe crude residue was chromatographed (silica gel with 5% ethyl acetate-95% hexane)

ORD record

ord-cc4ee3584a2946768ae2881b7b277ee8

Source dataset

uspto-grants-2005_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06875765B2