Water → HCID 14248988, compound

HRID 18027Notes

Reaction equation

HRID 18027 reaction equation
[CH3:1][C:2]([CH:6]1[O:10][O:9][C:7]1=[O:8])([CH2:4]O)[CH3:3].[H-].[Na+].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O>C1COCC1.ClCCl>[CH2:13]([O:10][C@@H:6]1[C:2]([CH3:1])([CH3:3])[CH2:4][O:9][C:7]1=[O:8])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 22244486D(-)-Pantolactone

Product 1

HCID 14248988HCID 14248988, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of D(−)-pantolactone (20.0 g, 153.7 mmol) and sodium hydride (4.4 g, 184.4 mmol) in anhydrous THF was stirred under an atmosphere of nitrogen at room temperature for 1 hour. The resultant mixture was treated with benzyl bromide (31.5 g, 184.4 mmol) and stirred at room temperature overnight. The product mixture was treated with water and diluted with dichloromethane. The organic extract was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum. The residue was subjected to purification on silica gel eluting with 0-5% methanol in dichloromethane gradient. Collection and concentration of appropriate fractions provided the title compound.

Workup

  1. stirringstirred at room temperature overnight
  2. extractionThe organic extract
  3. washwas washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue was subjected to purification on silica gel eluting with 0-5% methanol in dichloromethane gradient
  8. customCollection and concentration of appropriate fractions

Sources & evidence

ORD record
ord-523dccc1c3b84241ab3e653878ebd506
Source dataset
uspto-grants-2010_06
Patent number
US07741315B2

Reaction notes

Loading…