1-Naphthaleneboronic acid → alpha-Naphthaleneacetic acid, ethyl ester

HRID 1892466Notes

Reaction equation

HRID 1892466 reaction equation
[C:1]1(B(O)O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.CCCCCC.[C:20]([O:23][CH2:24][CH3:25])(=[O:22])[CH3:21]>>[C:1]1([CH2:21][C:20]([O:23][CH2:24][CH3:25])=[O:22])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 2545321-Naphthaleneboronic acidHCID 21226206Ethyl acetate hexane

Product 1

HCID 62428alpha-Naphthaleneacetic acid, ethyl ester

Procedure

Ethyl 1-naphthaleneacetate was prepared by the general experimental method from 1-naphthaleneboronic acid (172 mg, 1.00 mmol). After workup by column chromatography (hexane/ethyl acetate, 5:1), ethyl 1-naphthaleneacetate is obtained as a colourless liquid in a yield of 77% of theory. 1H NMR (600 MHz, CDCl3): δ=8.04 (d, J=8.3 Hz, 1H), 7.89 (d, J=8.1 Hz, 1H), 7.80-7.84 (m, 1H), 7.55-7.58 (m, 1H), 7.50-7.54 (m, 1H), 7.43-7.47 (m, 2H), 4.16-4.20 (m, 2H), 4.09 (s, 2H), 1.23-1.27 (m, 3H) ppm; 13C NMR (151 MHz, CDCl3): δ=171.7, 133.9, 132.2, 130.8, 128.8, 128.1, 128.0, 126.4, 125.8, 125.6, 123.9, 61.0, 39.4, 14.3 ppm; MS (70 eV), m/z (%): 214 (100) [M+], 141 (34), 115 (45), 89 (9), 63 (6); IR (NaCl): ν=3047 (w), 2981 (m), 1733 (s), 1173 (m), 1029 (m) cm−1, elemental analysis: (theor): C=78.48, H=6.59, (exp): C=78.35, H=6.86.

Sources & evidence

ORD record
ord-c180f843195c4025a34bd78ff7a3d786
Source dataset
uspto-grants-2013_08
Patent number
US08507688B2

Reaction notes

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