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

HRID 705322Notes

Reaction equation

HRID 705322 reaction equation
[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]

Participants

4

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-7ec2554b501743619a49137ca3109f58
Source dataset
uspto-grants-2015_11
Patent number
US09173939B2

Reaction notes

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