Toluene → 3-(1-trityl-1H-imidazol-4-yl)phenol

HRID 1176655노트

반응식

HRID 1176655 반응식
Br[C:2]1[N:3]=[CH:4][N:5]([C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=1.[OH:26][C:27]1[CH:28]=[C:29](OB(O)O)[CH:30]=[CH:31][CH:32]=1.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[C:7]([N:5]1[CH:6]=[C:2]([C:31]2[CH:32]=[C:27]([OH:26])[CH:28]=[CH:29][CH:30]=2)[N:3]=[CH:4]1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

참가 물질

6

반응물 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 27732744-Bromo-1-trityl-1H-imidazoleHCID 217081833-Hydroxyphenylboric acid

생성물 1

HCID 684993453-(1-trityl-1H-imidazol-4-yl)phenol

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
100 °C

실험 절차

A solution of 0.389 g of 4-bromo-1-trityl-1H-imidazole, 0.152 g of 3-hydroxyphenylboric acid and 10 ml of toluene is admixed with 3 ml of ethanol and 10 ml of aqueous 2N sodium carbonate solution. The mixture is purged with argon for 15 minutes and then 0.026 g of tetrakis(triphenylphosphine)palladium(0) is added. The reaction mixture is stirred at 100° C. for 48 hours, then cooled and poured onto 75 ml of aqueous saturated sodium hydrogencarbonate solution. The mixture is extracted three times with 75 ml of dichloromethane. The combined organic phases are washed with 75 ml of brine, dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a white solid from the residue by means of flash chromatography (SiO2 60F). Rf=0.13 (1:2 EtOAc-heptane); Rt=4.33.

후처리

  1. customThe mixture is purged with argon for 15 minutes
  2. addition0.026 g of tetrakis(triphenylphosphine)palladium(0) is added
  3. temperaturecooled
  4. additionpoured onto 75 ml of aqueous saturated sodium hydrogencarbonate solution
  5. extractionThe mixture is extracted three times with 75 ml of dichloromethane
  6. washThe combined organic phases are washed with 75 ml of brine
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated by evaporation

출처 및 근거

ORD 기록
ord-67c6051362804dabae51467f797412dd
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07842688B2

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