p-Toluenesulfonic acid → 2-(4-Methoxyphenyl)-4-(R)-undecyl-[1,3]dioxane

HRID 1636029노트

반응식

HRID 1636029 반응식
C1(C)C=CC(S(O)(=O)=O)=CC=1.CO[CH:14](OC)[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1.[OH:25][CH2:26][CH2:27][C@H:28]([OH:40])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39].C(OCC)(=O)C>CN(C)C=O>[CH3:22][O:21][C:18]1[CH:19]=[CH:20][C:15]([CH:14]2[O:40][C@H:28]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[CH2:27][CH2:26][O:25]2)=[CH:16][CH:17]=1

참가 물질

6

반응물 4

HCID 6101p-Toluenesulfonic acidHCID 8857Ethyl AcetateHCID 75140p-(Dimethoxymethyl)anisoleHCID 11791041(R)-1,3-dihydroxytetradecane

생성물 1

HCID 235566602-(4-Methoxyphenyl)-4-(R)-undecyl-[1,3]dioxane수율 99.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

p-Toluenesulfonic acid (152 mg, 0.80 mmol) and 4-methoxybenzaldehyde dimethylacetal (2.9 g, 16.0 mmol) was added to a solution of (R)-1,3-dihydroxytetradecane (1.85 g, 8.0 mnuol) in dimethylformamide (20 ml) and the mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure. The residue was diluted with ethyl acetate. The ethyl acetate layer was successively washed with saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution, dried over magnesium sulfate and then concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using cyclohexane:ethyl acetate=9:1 as the eluant to give the desired product (2.78 g, yield 99%).

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionThe residue was diluted with ethyl acetate
  3. washThe ethyl acetate layer was successively washed with saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by chromatography on a silica gel column

출처 및 근거

ORD 기록
ord-77fec4c6531c459cb074f813e19b88a2
출처 데이터셋
uspto-grants-2003_01
특허 번호
US06511965B2

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