2-Methoxynaphthalene → HCID 90095109, compound

HRID 627456Notes

Reaction equation

HRID 627456 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1.CC([O-])(C)C.[K+].[SiH:19]([CH2:24][CH3:25])([CH2:22][CH3:23])[CH2:20][CH3:21]>O1CCCC1>[CH2:20]([Si:19]([CH2:24][CH3:25])([CH2:22][CH3:23])[C:12]1[C:3]([O:2][CH3:1])=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:11]=1)[CH3:21]

Participants

5

Reactant 3

HCID 71192-MethoxynaphthaleneHCID 12052TriethylsilaneHCID 23665647Potassium tert-butoxide

Product 1

HCID 90095109HCID 90095109, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The reaction was conducted according to the General Procedure by heating 2-methoxynaphthalene (79 mg, 0.5 mmol, 1 equiv.), KOt-Bu (19.6 mg, 0.18 mmol, 0.35 equiv.) and Et3SiH (319 microliters, 2.0 mmol, 4 equiv.) in 1 mL of tetrahydrofuran for 48 hours at 65° C. After aqueous work up, the crude reaction mixture was purified by chromatography on silica eluting with hexanes (isochratic) to obtain 79 mg (58%) of the title compound as colourless oil. 1H NMR (500 MHz, THF-d8) δ 7.84 (s, 1H), 7.78-7.73 (d, 1H), 7.73-7.68 (d, 1H), 7.38 (ddd, J=8.2, 6.8, 1.3 Hz, 1H), 7.27 (ddd, J=8.1, 6.8, 1.2 Hz, 1H), 7.15 (s, 1H), 3.90 (s, 3H), 1.01-0.90 (m, 9H), 0.68-0.53 (m, 6H). 13C NMR (126 MHz, THF-d8) δ 163.03, 137.88, 136.83, 130.10, 128.58, 128.09, 127.29, 127.21, 124.03, 104.57, 55.25, 8.02, 7.48. HRMS: [C17H24OSi] calculated 272.1608, measured 272.1596. The HSQC spectra of the 2-methoxynaphthalene and its reaction product are provided in FIG. 5.

Workup

  1. customAfter aqueous work up, the crude reaction mixture
  2. customwas purified by chromatography on silica eluting with hexanes (isochratic)

Sources & evidence

ORD record
ord-48fa69cfc567438dbf609514cb320b66
Source dataset
uspto-grants-2016_04
Patent number
US09309269B2

Reaction notes

Loading…