Triethylsilane → (1,1'-Biphenyl)-2-ol

HRID 627451Notes

Reaction equation

HRID 627451 reaction equation
[CH2:1]([Si:3]([CH2:19][CH3:20])([CH2:17][CH3:18])[C:4]1[C:9]2[O:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[C:8]=2[CH:7]=[CH:6][CH:5]=1)[CH3:2].CC([O-])(C)C.[K+].[SiH](CC)(CC)CC>C1(C)C=CC=CC=1>[C:12]1([C:8]2[CH:7]=[CH:6][CH:5]=[CH:4][C:9]=2[OH:10])[CH:11]=[CH:16][CH:15]=[CH:14][CH:13]=1.[CH2:17]([Si:3]([CH2:1][CH3:2])([CH2:19][CH3:20])[C:4]1[CH:5]=[CH:6][CH:7]=[C:8]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:11]=2)[C:9]=1[OH:10])[CH3:18].[CH2:17]([Si:3]([CH2:1][CH3:2])([CH2:19][CH3:20])[C:4]1[CH:9]=[C:8]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[OH:10])[CH:7]=[CH:6][CH:5]=1)[CH3:18]

Participants

7

Reactant 3

HCID 12052TriethylsilaneHCID 23665647Potassium tert-butoxideHCID 86714195HCID 86714195, compound

Product 3

HCID 7017(1,1'-Biphenyl)-2-olYield 35%HCID 867141933-(Triethylsilyl)biphenyl-2-olYield 26%HCID 867141942-(3-Triethylsilylphenyl)phenolYield 12%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The reaction was conducted according to the General Procedure by heating 4-Et3Si-dibenzofuran (3, 141 mg, 0.5 mmol, 1 equiv.), KOt-Bu (112 mg, 1 mmol, 2 equiv.) and Et3SiH (401 microliters, 2.5 mmol, 5 equiv.) in 2 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 isolate 2-phenylphenol (2, 30 mg, 0.177 mmol, 35%), 2-triethylsilyl-6-phenylphenol (5, 37 mg, 0.134 mmol, 26%), 2-(3-triethylsilylphenyl)phenol (6, 17 mg, 0.063 mmol, 12%). Quantities of unconsumed 3 as well as products 1, 4 and 7 were obtained using post-chromatography GC-FID analysis of the corresponding mixed fractions.

Workup

  1. customAfter acidic aqueous work up, the crude reaction mixture
  2. customwas purified by chromatography on silica

Sources & evidence

ORD record
ord-e7baaa019cd2441a84a34c9d994aa045
Source dataset
uspto-grants-2016_04
Patent number
US09309269B2

Reaction notes

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