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Bi(OTf)3 → (S)-1-chloro-3-(4-(2-(4-((R)-2,3-dihydroxypropoxy)phenyl)propan-2-yl)phenoxy)propan-2-yl acetate

HRID 705322
ノート
印刷プレビュー

反応式

HRID 705322 の反応式
[C:1]([O:4][C@@H:5]([CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][C@H:27]3[CH2:31][O:30]C(C)(C)[O:28]3)=[CH:21][CH:20]=2)([CH3:18])[CH3:17])=[CH:12][CH:11]=1)[CH2:6][Cl:7])(=[O:3])[CH3:2].[O-]S(C(F)(F)F)(=O)=O.[Bi+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O>C(#N)C>[C:1]([O:4][C@@H:5]([CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][C@H:27]([OH:28])[CH2:31][OH:30])=[CH:21][CH:20]=2)([CH3:18])[CH3:17])=[CH:12][CH:11]=1)[CH2:6][Cl:7])(=[O:3])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 9917655Bi(OTf)3HCID 117689799(S)-1-chloro-3-(4-(2-(4-(((S)-2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)phenyl)propan-2-yl)phenoxy)propan-2-yl acetate

生成物 1

HCID 86293252(S)-1-chloro-3-(4-(2-(4-((R)-2,3-dihydroxypropoxy)phenyl)propan-2-yl)phenoxy)propan-2-yl acetate収率 86%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a solution of crude (S)-1-chloro-3-(4-(2-(4-(((S)-2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)phenyl)propan-2-yl)phenoxy)propan-2-yl acetate in anhydrous acetonitrile (8.0 mL) was added bismuth triflate (300 mg, 0.46 mmol) in one portion. After 0.5 h, the reaction mixture was partitioned twice with sodium bicarbonate and ethyl acetate. The organic phased were combined, dried over anhydrous magnesium sulfate, and filtered. Solvents were evaporated, and the resulting crude material was purified by silica gel flash chromatography (eluent: 2% to 5% methanol in dichloromethane) to provide the title compound (734 mg, 86%) as a sticky solid.

後処理

  1. customthe reaction mixture was partitioned twice with sodium bicarbonate and ethyl acetate
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customSolvents were evaporated
  5. customthe resulting crude material was purified by silica gel flash chromatography (eluent: 2% to 5% methanol in dichloromethane)

出典と根拠

ORDレコード
ord-7ec2554b501743619a49137ca3109f58
出典データセット
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09173939B2

反応ノート

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