Water → {2',3',5',6'-Tetramethyl-4'-[3-(methylsulfonyl)propoxy]biphenyl-3-yl}methanol

HRID 15635노트

반응식

HRID 15635 반응식
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([C:9]2[C:14]([CH3:15])=[C:13]([CH3:16])[C:12]([OH:17])=[C:11]([CH3:18])[C:10]=2[CH3:19])[CH:6]=[CH:7][CH:8]=1.CC1C=CC(S(O[CH2:31][CH2:32][CH2:33][S:34]([CH3:37])(=[O:36])=[O:35])(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:19][C:10]1[C:11]([CH3:18])=[C:12]([O:17][CH2:31][CH2:32][CH2:33][S:34]([CH3:37])(=[O:36])=[O:35])[C:13]([CH3:16])=[C:14]([CH3:15])[C:9]=1[C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([CH2:2][OH:1])[CH:4]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 22732325(3-(Methylsulfonyl)propyl 4-methylbenzenesulfonateHCID 593426133'-(Hydroxymethyl)-2,3,5,6-tetramethylbiphenyl-4-ol

생성물 1

HCID 59342583{2',3',5',6'-Tetramethyl-4'-[3-(methylsulfonyl)propoxy]biphenyl-3-yl}methanol수율 85%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

To a solution of 3′-(hydroxymethyl)-2,3,5,6-tetramethylbiphenyl-4-ol (0.616 g, 2.40 mmol) and 3-(methylsulfonyl)propyl 4-methylbenzenesulfonate (1.05 g, 3.60 mol) in N,N-dimethylformamide (5 mL) was added potassium carbonate (0.597 g, 4.32 mmol), and the mixture was stirred at 90° C. for 12 hr under nitrogen atmosphere. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed successively with 1 M aqueous sodium hydroxide solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=40:60-80:20), and the obtained crystals were recrystallized from heptane-ethyl acetate to give the title compound (0.577 g, yield 85%) as colorless crystals.

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed successively with 1 M aqueous sodium hydroxide solution and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=40:60-80:20)
  6. customthe obtained crystals were recrystallized from heptane-ethyl acetate

출처 및 근거

ORD 기록
ord-1be4d2f13b8c4cafa47eb259028bc0dc
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732626B2

반응 노트

불러오는 중…