Dibenzofuran → HCID 90094861, compound

HRID 627450Notes

Reaction equation

HRID 627450 reaction equation
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.C[C:15]([O-])([CH3:17])C.[K+].[SiH:20]([CH2:25][CH3:26])([CH2:23][CH3:24])[CH2:21][CH3:22]>C1(C)C=CC=CC=1>[CH2:21]([Si:20]([CH2:15][CH3:17])([CH2:23][CH3:24])[C:13]1[CH:12]=[CH:11][CH:10]=[C:8]([C:9]2[CH:5]=[CH:4][CH:3]=[C:2]([Si:20]([CH2:25][CH3:26])([CH2:23][CH3:24])[CH2:21][CH3:22])[CH:1]=2)[C:7]=1[OH:6])[CH3:22]

Participants

5

Reactant 3

HCID 568DibenzofuranHCID 12052TriethylsilaneHCID 23665647Potassium tert-butoxide

Product 1

HCID 90094861HCID 90094861, compoundYield 1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The title compound was prepared according to General Procedure by heating dibenzofuran (1, 840 mg, 5.0 mmol, 1 equiv.) with KOt-Bu (1.12 g, 10 mmol, 2 equiv.) and Et3SiH (4.0 ml, 25 mmol, 5 equiv.) in 20 ml of toluene for 20 hours at 100° C. After acidic aqueous work up, the crude reaction mixture was purified by chromatography on silica using hexanes and hexanes-ether (10:1) to give, among other isolated products, 20 mg (0.05 mmol, 1%) of 7. Data for (7): oily solid 1H-NMR (300 MHz, CDCl3): δ 7.53-7.44 (m, 2Har), 7.46-7.44 (m, 2Har), 7.36 (dd, J=1.5, 7.5 Hz, 1Har), 7.23 (dd, J=1.5, 7.5 Hz, 1Har), 6.98 (t, J=7 Hz, 1Har), 5.42 (s, 1H, OH), 1.01-0.96 (m, 18H, 6CH3) 0.91-0.77 (m, 15H, 6CH2). 13C NMR (75 MHz, CDCl3): δ 157.37, 139.45, 136.61, 135.87, 135.09, 133.86, 131.38, 129.57, 128.71, 127.55, 122.97, 120.36, 7.80, 7.57, 3.69, 3.46. HRMS: [C24H38OSi2] calculated 398.2461; measured 396.2470.

Workup

  1. customThe title compound was prepared
  2. customAfter acidic aqueous work up, the crude reaction mixture
  3. customwas purified by chromatography on silica

Sources & evidence

ORD record
ord-5f96548ae5bd4478b527b2135ddd32a0
Source dataset
uspto-grants-2016_04
Patent number
US09309269B2

Reaction notes

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