2-Methoxynaphthalene → HCID 90095109, compound

HRID 1467426Notes

Reaction equation

HRID 1467426 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.

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-7bcd41a17fac4f198b86c779e33f2481
Source dataset
uspto-grants-2015_04
Patent number
US09000167B2

Reaction notes

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