Water → 1-{5'-[2-(3,4-Bis(hydroxymethyl)phenyl)ethyl]-2'-methyl-2-propylbiphenyl-4-yl}propan-1-one

HRID 584319노트

반응식

HRID 584319 반응식
[CH2:1]([C:3]1([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[C:19]([CH3:20])=[CH:18][CH:17]=[C:16]([CH2:21][CH2:22][C:23]4[CH:28]=[CH:27][C:26]([CH2:29][OH:30])=[C:25]([CH2:31][OH:32])[CH:24]=4)[CH:15]=3)=[C:10]([CH2:33][CH2:34][CH3:35])[CH:9]=2)OCC[O:4]1)[CH3:2].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>CC(C)=O>[OH:32][CH2:31][C:25]1[CH:24]=[C:23]([CH2:22][CH2:21][C:16]2[CH:17]=[CH:18][C:19]([CH3:20])=[C:14]([C:11]3[CH:12]=[CH:13][C:8]([C:3](=[O:4])[CH2:1][CH3:2])=[CH:9][C:10]=3[CH2:33][CH2:34][CH3:35])[CH:15]=2)[CH:28]=[CH:27][C:26]=1[CH2:29][OH:30]

참가 물질

6

반응물 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 22345598HCID 22345598, 화합물

생성물 1

HCID 223455891-{5'-[2-(3,4-Bis(hydroxymethyl)phenyl)ethyl]-2'-methyl-2-propylbiphenyl-4-yl}propan-1-one수율 50%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

640 mg (1.4 mmol) of (4-{2-[4′-(2-ethyl[1,3]dioxolan-2-yl)-6-methyl-2′-propylbiphenyl-3-yl]ethyl}-2-hydroxymethylphenyl)methanol are placed in 15 ml of acetone and 15 ml of water in a round-bottomed flask. A spatula-tip of p-toluenesulfonic acid is added and the solution is refluxed for 2 hours 30 minutes. At room temperature, it is poured into saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic phase is dried over magnesium sulfate, filtered and then evaporated. The residue obtained is purified by chromatography on a column of silica eluted with a mixture of heptane and ethyl acetate (30/70). 300 mg (50%) of the expected product are obtained in the form of a colorless oil.

후처리

  1. temperaturethe solution is refluxed for 2 hours 30 minutes
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue obtained
  7. customis purified by chromatography on a column of silica
  8. washeluted with a mixture of heptane and ethyl acetate (30/70)

출처 및 근거

ORD 기록
ord-5b6caba6a0f54ddb9cb5a1b54f77e7af
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06924400B2

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