Water → (S)-3-(4-{3-[4-(3-bromo-propyl)-phenoxy]-propyl}-phenoxy)-propane-1,2-diol

HRID 882926노트

반응식

HRID 882926 반응식
[Br:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:29]=[CH:28][C:8]([O:9][CH2:10][CH2:11][CH2:12][C:13]2[CH:27]=[CH:26][C:16]([O:17][CH2:18][C@@H:19]3[CH2:23][O:22]C(C)(C)[O:20]3)=[CH:15][CH:14]=2)=[CH:7][CH:6]=1.C(O)(C(F)(F)F)=O.O>C(Cl)Cl>[Br:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][C:8]([O:9][CH2:10][CH2:11][CH2:12][C:13]2[CH:27]=[CH:26][C:16]([O:17][CH2:18][C@@H:19]([OH:20])[CH2:23][OH:22])=[CH:15][CH:14]=2)=[CH:28][CH:29]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 67029042(R)-4-(4-{3-[4-(3-bromo-propyl)-phenoxy]-propyl}-phenoxymethyl)-2,2-dimethyl-[1,3]dioxolane

생성물 1

HCID 67028182(S)-3-(4-{3-[4-(3-bromo-propyl)-phenoxy]-propyl}-phenoxy)-propane-1,2-diol

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of (R)-4-(4-{3-[4-(3-bromo-propyl)-phenoxy]-propyl}-phenoxymethyl)-2,2-dimethyl-[1,3]dioxolane (5.0 g, 10.8 mmol) in DCM (50 mL) is added TFA (2.0 mL, 26.9 mmol) dropwise followed by water (2.0 mL) and the reaction mixture is stirred at RT overnight. The solvent is removed in vacuo and the residue is treated with aqueous sodium hydrogen carbonate solution. The mixture is extracted with EtOAc (3×200 mL) and the combined organic portions are washed with water, brine, dried over Na2SO4 and concentrated in vacuo. Recrystallizisation of the residue from diethyl ether-hexane affords the title compound as white solid.

후처리

  1. customThe solvent is removed in vacuo
  2. additionthe residue is treated with aqueous sodium hydrogen carbonate solution
  3. extractionThe mixture is extracted with EtOAc (3×200 mL)
  4. washthe combined organic portions are washed with water, brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-752ea989c16b46fb824c2631434aeb73
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08236808B2

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