Water → HCID 561798, compound

HRID 1842117Notes

Reaction equation

HRID 1842117 reaction equation
[CH2:1]([Li])CCC.[I-].C[S+](C)C.[CH2:11]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:12]1[O:14][CH2:13]1.O>CCCCCC.O1CCCC1>[CH2:16]([O:15][CH2:11][CH:12]([OH:14])[CH:13]=[CH2:1])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 962WaterHCID 75127Trimethylsulfonium iodideHCID 94247Benzyl glycidyl etherHCID 178418339Butyllithium

Product 1

HCID 561798HCID 561798, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

A 2.64 M solution of n-butyllithium in hexane (35.7 mL) was added to a solution of trimethylsulfonium iodide (19.9 g) in tetrahydrofuran (300 mL) at −25° C. The mixture was stirred at the same temperature for 30 minutes. Benzyl glycidyl ether (5.00 mL) was added to the reaction solution at the same temperature, and then the mixture was warmed to room temperature over two hours and 50 minutes. Water was added to the reaction solution, followed by extraction with diethyl ether. The organic layer was dried over anhydrous magnesium sulfate. The drying agent was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (6.98 g).

Workup

  1. extractionfollowed by extraction with diethyl ether
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationThe drying agent was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d4defe5e3fa54f9da523e5a4bdf05e46
Source dataset
uspto-grants-2015_02
Patent number
US08946211B2

Reaction notes

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