Benzophenone → 1,1,2-Triphenylethanol

HRID 1713386노트

반응식

HRID 1713386 반응식
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Mg].[C:10]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>CCOCC>[C:11]1([C:10]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([OH:17])[CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

참가 물질

5

반응물 3

HCID 3102BenzophenoneHCID 7498Benzyl BromideHCID 5462224Magnesium

생성물 1

HCID 2450131,1,2-Triphenylethanol수율 65%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매3회

실험 절차

To a suspension of Mg (1.7 g, 0.07 mol) in dry ether (25 mL) was added a solution of benzyl bromide (10 mL, 1.5 equ.) in dry ether (25 mL) drop-wise and allowed to stir at RT for 1 h. By the time all magnesium was dissolved and the reaction mixture was cooled to 0° C. To this was added a solution of benzophenone (10 g, 0.05 mol) in dry ether (25 mL) and allowed to stir at RT for 5 h. The progress of the reaction was followed by TLC and when it was ready the reaction mixture was quenched with saturated NH4Cl solution, extracted with ether (100 mL), washed with brine, dried and concentrated under vacuum. The crude product was purified by column chromatography on silica gel (10% ethyl acetate in pet. ether) to give the title compound (9.6 g, 65%) as a white solid. TLC: Pet. ether/EtOAc, 9:1, Rf=0.4

후처리

  1. temperaturethe reaction mixture was cooled to 0° C
  2. stirringto stir at RT for 5 h
  3. customwas quenched with saturated NH4Cl solution
  4. extractionextracted with ether (100 mL)
  5. washwashed with brine
  6. customdried
  7. concentrationconcentrated under vacuum
  8. customThe crude product was purified by column chromatography on silica gel (10% ethyl acetate in pet. ether)

출처 및 근거

ORD 기록
ord-6f723f26a43149e98520440d64561a1e
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07795270B2

반응 노트

불러오는 중…