Chlorotrimethylsilane → HCID 136377632, 화합물

HRID 1581779노트

반응식

HRID 1581779 반응식
[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

참가 물질

6

반응물 4

HCID 6397ChlorotrimethylsilaneHCID 6456Trityl chlorideHCID 8471TriethylamineHCID 819511o-(1H-pyrazol-3-yl)phenol

생성물 1

HCID 136377632HCID 136377632, 화합물수율 42.7%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-978d1698c8654dbcb90811145cf509c8
출처 데이터셋
uspto-grants-2004_05
특허 번호
US06730792B2

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