Pyridine → HCID 57081818, compound

HRID 1609177Notes

Reaction equation

HRID 1609177 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]([OH:16])=[O:15])=[CH:4][CH:3]=1.N1C=CC=CC=1.[CH3:23][Si:24]([CH:27](O)[CH3:28])([CH3:26])[CH3:25].C1(N=C=NC2CCCCC2)CCCCC1>C(#N)C>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]([O:16][CH2:28][CH2:27][Si:24]([CH3:26])([CH3:25])[CH3:23])=[O:15])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 10868DicyclohexylcarbodiimideHCID 815682-(4-Methylphenyl)benzoic acidHCID 124478981-(Trimethylsilyl)ethanol

Product 1

HCID 57081818HCID 57081818, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The starting material can be obtained, for example, as follows: 14.2 g of 4-methyl-2'-carboxybiphenyl (EP 253,310) are dissolved in 60 ml of acetonitrile and 10.7 ml of pyridine and 11.4 ml of trimethylsilylethanol are added. The mixture is treated at 0° with 15.1 g of dicyclohexylcarbodiimide and stirred at this temperature for 3 hours. After this, the reaction mixture is evaporated in a high vacuum, the residue is treated with ether, and dicyclohexylurea is filtered off. After flash chromatography (ethyl acetate/hexane 95:5), 4-methyl-2'-(trimethylsilylethoxycarbonyl)biphenyl is obtained as a slightly yellowish oil. (TLC: ethyl acetate/hexane 95:5) Rf : 0.42. 312 mg of 4-methyl-2'-(trimethylsilylethoxycarbonyl)biphenyl, 178 mg of N-bromosuccinimide, 5 mg of azoisobutyronitrile and 15 ml of carbon tetrachloride are heated to reflux for one hour. After cooling, the mixture is evaporated. Flash chromatography (ethyl acetate/hexane 95:5) yields 4-bromomethyl-2'-(trimethylsilylethoxycarbonyl)biphenyl as a slightly yellowish oil. 1H-NMR (CFCl3): 0 ppm (s, 9H), 0.7 ppm (t, 2H), 4.5 ppm (s, 2H), 7.1-8 ppm aromatics.

Workup

  1. customAfter this, the reaction mixture is evaporated in a high vacuum
  2. additionthe residue is treated with ether, and dicyclohexylurea
  3. filtrationis filtered off

Sources & evidence

ORD record
ord-8eccf96d57744186b5f87ad220ab9ee5
Source dataset
uspto-grants-1995_03
Patent number
US05399578

Reaction notes

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