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

HRID 882926ノート

反応式

HRID 882926 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-752ea989c16b46fb824c2631434aeb73
出典データセット
uspto-grants-2012_08
特許番号
US08236808B2

反応ノート

読み込み中…