2,3-Dihydrofuran → 1,3-O-di-(t-butyldimethylsilyl)-2-O-tetrahydrofuranylglycerol

HRID 376414Notes

Reaction equation

HRID 376414 reaction equation
[Si:1]([O:8][CH2:9][CH:10]([CH2:12][O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[OH:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[O:38]1[CH:42]=[CH:41][CH2:40][CH2:39]1>O1CCOCC1>[Si:1]([O:8][CH2:9][CH:10]([CH2:12][O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:15])[CH3:16])[O:11][CH:39]1[CH2:40][CH2:41][CH2:42][O:38]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 709342,3-DihydrofuranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 107580914,8-Dioxa-3,9-disilaundecan-6-ol, 2,2,3,3,9,9,10,10-octamethyl-

Product 1

HCID 193612641,3-O-di-(t-butyldimethylsilyl)-2-O-tetrahydrofuranylglycerolYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

In dioxane was dissolved 3.45 g (11 mmol) of 1,3-O-di-(t-butyldimethylsilyl)glycerol followed by addition of 3.03 g (12 mmol) of pyridinium p-toluenesulfonate. To this suspension was added 16.5 ml (22 mmol) of dihydrofuran gradually under ice-cooling and the mixture was stirred for 1 hour. After return to ambient temperature, the mixture was allowed to react overnight. After completion of the reaction, the solvent was distilled off and the residue was treated with methylene chloride and saturated aqueous sodium hydrogen carbonate solution. The methylene chloride layer was washed with water, dried, and concentrated to provide 4.25 g (100%) of 1,3-O-di-(t-butyldimethylsilyl)-2-O-tetrahydrofuranylglycerol.

Workup

  1. temperaturecooling
  2. customto ambient temperature
  3. customto react overnight
  4. customAfter completion of the reaction
  5. distillationthe solvent was distilled off
  6. additionthe residue was treated with methylene chloride and saturated aqueous sodium hydrogen carbonate solution
  7. washThe methylene chloride layer was washed with water
  8. customdried
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-452df22ba2ee4de9a642527daadbff43
Source dataset
uspto-grants-2000_02
Patent number
US06020317

Reaction notes

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