Chlorotrimethylsilane → HCID 136377632, compound

HRID 1581779Notes

Reaction equation

HRID 1581779 reaction equation
[NH:1]1[C:5]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[OH:12])=[CH:4][CH:3]=[N:2]1.C(N(CC)CC)C.Cl[Si](C)(C)C.[C:25](Cl)([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(#N)C>[C:25]([N:1]1[C:5]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[OH:12])=[CH:4][CH:3]=[N:2]1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 6456Trityl chlorideHCID 8471TriethylamineHCID 8195112-(1H-Pyrazol-3-yl)phenol

Product 1

HCID 136377632HCID 136377632, compoundYield 42.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-(pyrazol-5-yl)phenol (Catalan, et al., J. Am. Chem. Soc., 114(13):5039-48, 1992, 10 mmol, 1.60 g), triethylamine (40.0 mmol, 5.6 ml), and acetonitrile (55 ml) is cooled in an ice bath under N2 and treated dropwise with chlorotrimethylsilane (12.0 mmol, 1.52 ml). After the addition is complete, the cold bath is removed and the reaction mixture stirred at ambient temperature for 1 hour. The reaction mixture is then treated with trityl chloride (10.0 mmol, 2.78 g) and stirred at ambient temperature overnight, followed by refluxing for 1 hour. The reaction mixture is concentrated, treated with saturated aqueous sodium bicarbonate, and extracted with ethyl acetate (3×50 ml). The extracts are dried over magnesium sulfate and concentrated to a viscous oil. The oil is crystallized from 20% ethyl acetate/hexane to give 1.72 g of N-trityl-2-(pyrazol-5-yl)phenol.

Workup

  1. temperatureis cooled in an ice bath under N2
  2. additionAfter the addition
  3. customthe cold bath is removed
  4. stirringstirred at ambient temperature overnight
  5. temperatureby refluxing for 1 hour
  6. concentrationThe reaction mixture is concentrated
  7. additiontreated with saturated aqueous sodium bicarbonate
  8. extractionextracted with ethyl acetate (3×50 ml)
  9. dry with materialThe extracts are dried over magnesium sulfate
  10. concentrationconcentrated to a viscous oil
  11. customThe oil is crystallized from 20% ethyl acetate/hexane

Sources & evidence

ORD record
ord-978d1698c8654dbcb90811145cf509c8
Source dataset
uspto-grants-2004_05
Patent number
US06730792B2

Reaction notes

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