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

HRID 724759Notes

Reaction equation

HRID 724759 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-25795163f9fd40cc8dca13b23c2206a6
Source dataset
uspto-grants-1998_01
Patent number
US05705188

Reaction notes

Loading…