Benzofuran → HCID 90094819, compound

HRID 1467432Notes

Reaction equation

HRID 1467432 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[CH:2]1.CC([O-])(C)C.[K+].[SiH:16]([CH2:21][CH3:22])([CH2:19][CH3:20])[CH2:17][CH3:18]>O1CCCC1>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[Si:16]([CH2:21][CH3:22])([CH2:19][CH3:20])[CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 9223BenzofuranHCID 12052TriethylsilaneHCID 23665647Potassium tert-butoxide

Product 1

HCID 90094819HCID 90094819, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The reaction was conducted according to the General Procedure by heating benzofuran (59 mg, 0.5 mmol, 1 equiv.), KOt-Bu (19.6 mg, 0.18 mmol, 0.35 equiv.) and Et3SiH (239 microliters, 1.5 mmol, 3 equiv.) in 1 mL of tetrahydrofuran for 45 hours at 60° C. After aqueous work up, the crude reaction mixture was purified by chromatography on silica eluting with hexanes (isochratic) to obtain 44 mg (38%) of the title compound as a colourless oil. 1H NMR (500 MHz, Acetone-d6) δ 7.64 (ddd, J=7.7, 1.3, 0.7 Hz, 1H), 7.53 (dd, J=8.2, 0.9 Hz, 1H), 7.30 (ddd, J=8.3, 7.2, 1.3 Hz, 1H), 7.22 (ddd, J=7.7, 7.2, 1.0 Hz, 1H), 7.16 (d, J=1.0 Hz, 1H), 1.09-0.98 (m, 9H), 0.92-0.84 (m, 6H). The HSQC spectrum of this reaction product as provided in FIG. 13.

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-7d7bd8e9965e4e0fb2047f49a95c2fe8
Source dataset
uspto-grants-2015_04
Patent number
US09000167B2

Reaction notes

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