Water → HCID 86630165, compound

HRID 731127Notes

Reaction equation

HRID 731127 reaction equation
FC(F)(F)[S:3]([O-])(=O)=O.[Yb+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O.[C:26]1(S)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[O:33]1[C@H:42]([CH3:43])[C@H:34]1[C:35]([O:37][CH2:38][CH2:39][CH2:40][CH3:41])=O.O>C(Cl)Cl>[OH:33][C@@H:34]([C@H:42]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH3:43])[C:35]([O:37][CH2:38][CH2:39][CH2:40][CH3:41])=[S:3]

Participants

6

Reactant 4

HCID 962WaterHCID 7969ThiophenolHCID 2733225Ytterbium triflateHCID 11182755HCID 11182755, compound

Product 1

HCID 86630165HCID 86630165, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ytterbium trifluoromethanesulfonate [Yb(OTf)3] (196 mg) and thiophenol (0.032 mL) were sequentially added at room temperature to a solution of n-butyl (2S,3R)-2,3-epoxybutyrate (50 mg) in methylene chloride (3.0 mL), and the mixture was stirred at the same temperature for 24 hours. The reaction mixture was added to water (20 mL), and extracted with chloroform (20 mL×3). The organic layers were combined, and the combined organic layer was dried over sodium sulfate anhydrate and concentrated under reduced pressure. The residue was purified through preparative thin-layer chromatography (n-hexane/ethyl acetate=5/1), to thereby yield colorless oil (69 mg, 81.3%).

Workup

  1. extractionextracted with chloroform (20 mL×3)
  2. dry with materialthe combined organic layer was dried over sodium sulfate anhydrate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified through preparative thin-layer chromatography (n-hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-faeb46b8734e40a1898e97e11ac33f5f
Source dataset
uspto-grants-2009_09
Patent number
US07582791B2

Reaction notes

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