Structure of 67247-13-6
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 67247-13-6 |
Formula : | C11H10O2 |
M.W : | 174.20 |
SMILES Code : | COC1=CC=C2C(=C1)C(=CC=C2)O |
MDL No. : | MFCD01314215 |
InChI Key : | KUKJAAZDXZNNPD-UHFFFAOYSA-N |
Pubchem ID : | 599942 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With 2,6-di-tert-butyl-4-methylpyridine; In dichloromethane; for 12.0h;Reflux; | In a reactor, 2.7 g of 7-methoxy-1-naphthol, 1.1 eq. of triflic anhydride and 1.1 eq. of 2,6-di-tert-butyl-4-methyl-pyridine are introduced into dichloromethane (45 ml). The mixture is heated at reflux for 12 hours and then filtered, and the liquors are washed with 1N HCl solution and then with saturated NaCl solution. The organic phase is evaporated and the residue obtained is purified by chromatography on silica gel (eluant: CH2Cl2/methyl-cyclohexane 1/9) to yield the title product in the form of an oil in a yield of 91% and with a chemical purity of more than 99%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 3 7-Methoxy-1-naphthalenol Mp 105-107 (a mp of 103-105 is given by A. J. Shand and R. H. Thomson, Tetrahedron, 19, 1919 (1963)). Calcd. for C11 H10 O2: C, 75.84; H, 5.79; Found C, 75.49; H, 5.85, and |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 2,6-dimethylpyridine; In dichloromethane; at 0 - 20℃; | To a solution of 25 g 7-methoxy-l-naphthol in 500 mL DCM at 00C was added 26.14 g2,6-diemthylpyridine followed by 45.52 g fer?-butyl(dimethyl)silyl trifluoromethanesulfonate.The mixture was allowed to warm up to room temperature overnight and worked up with water and DCM. The crude product was purified with SGC using hexanes to give the title compound.1H NMR (CDCl3, 500 MHz) delta: 7.73 (d, 8.5 Hz, IH), 7.53 (d, 2.5 Hz, IH)5 7.42 (d, 8.0 Hz, IH)5 7.21 (t, 8.0 Hz5 IH)5 7.16 (dd, 9.0 & 2.5 Hz5 IH), 6.88 (d5 7.5 Hz, IH)5 3.95 (s5 3H)5 1.15 (s5 9H)50.31 (S5 6H). |
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