Methanol → HCID 20401795, compound

HRID 1980523Notes

Reaction equation

HRID 1980523 reaction equation
[C:1]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][C:4]([Si:7]([CH3:12])([CH3:11])[CH:8](Cl)[CH3:9])=[CH:3][CH:2]=1.[K].[NH:20]1[CH:24]=[N:23][CH:22]=[N:21]1.CO>CN(C)C=O.O.ClCCl>[C:1]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][C:4]([Si:7]([CH3:12])([CH3:11])[CH:8]([N:20]2[CH:24]=[N:23][CH:22]=[N:21]2)[CH3:9])=[CH:3][CH:2]=1

Participants

7

Reactant 3

HCID 887MethanolHCID 20401742HCID 20401742, compoundHCID 534465811,2,4-Triazole potassium

Product 1

HCID 20401795HCID 20401795, compoundYield 13.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2.50 g (7.46 mmol) of 82% pure (1,1'-biphenyl-4-yl)dimethyl-1-chloroethylsilane and 1.60 g (15 mmol) of 1H-1,2,4-triazole potassium salt in 15 ml of dimethylformamide was stirred at 50° for 64 hours, cooled, diluted with water, and extracted with ether. The ether extracts were washed with water and brine, dried over magnesium sulfate, and evaporated to leave a viscous oil. Chromatography over silica gel eluting with 2% methanol in dichloromethane gave 0.30 g (13%) of the title compound as a pale yellow oil: nmr (CDCl3) 0.38 and 0.42 (total 6H, two equal s), 1.6 (3H, d, J=7 Hz), 4.2 (1H, q, J=7 Hz), 7.3-7.8 (9H, m), 7.9 (1H, s) and 8.0 (1H, s).

Workup

  1. temperaturecooled
  2. extractionextracted with ether
  3. washThe ether extracts were washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customto leave a viscous oil

Sources & evidence

ORD record
ord-01a983b83e2d4092b650d8a1804ac584
Source dataset
uspto-grants-1985_04
Patent number
US04510136

Reaction notes

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