Hydrochloric Acid → HCID 13474665, compound

HRID 1980527Notes

Reaction equation

HRID 1980527 reaction equation
[C:1]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:6]=[CH:5][C:4]([Si:7]([CH3:18])([O:14]C(C)C)[CH2:8][N:9]2[CH:13]=[N:12][CH:11]=[N:10]2)=[CH:3][CH:2]=1.Cl.O.O1CCCC1>CCOCC>[C:1]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:2]=[CH:3][C:4]([Si:7]([OH:14])([CH3:18])[CH2:8][N:9]2[CH:13]=[N:12][CH:11]=[N:10]2)=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8028TetrahydrofuranHCID 13474661HCID 13474661, compound

Product 1

HCID 13474665HCID 13474665, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 3.0 g (8.9 mmol) of (1,1'-biphenyl-4-yl)methyl(2-propoxy)(1H-1,2,4-triazol-1-ylmethyl)silane, 3 ml of concentrated hydrochloric acid, 10 ml of water, and 10 ml of tetrahydrofuran was stirred at room temperature overnight. The resulting solution was diluted with ether, washed with saturated aqueous sodium bicarbonate, water, and brine, dried over magnesium sulfate, and evaporated to leave 2.3 g of viscous oil. Chromatography over silica gel, eluting with hexane followed by ether, provided 1.1 g (42%) of the title compound as a viscous oil that solidified on standing: m.p. 97°-99°; nmr (CDCl3) 0.5 (3H, s), 3.9 (2H, s), 5.2 (1H, broad s), 7.3-7.8 (9H, m), 7.9 (1H, s), 8.0 (1H, s).

Workup

  1. washwashed with saturated aqueous sodium bicarbonate, water, and brine
  2. dry with materialdried over magnesium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-b81dd2dd999846b7a7b3b9d78d3973d6
Source dataset
uspto-grants-1985_04
Patent number
US04510136

Reaction notes

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