Tetrabutylammonium Fluoride → 2-O-tetrahydrofuranylglycerol

HRID 724760Notes

Reaction equation

HRID 724760 reaction equation
[Si]([O:8][CH2:9][CH:10]([CH2:17][O:18][Si](C(C)(C)C)(C)C)[O:11][CH:12]1[CH2:16][CH2:15][CH2:14][O:13]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[O:13]1[CH2:14][CH2:15][CH2:16][CH:12]1[O:11][CH:10]([CH2:9][OH:8])[CH2:17][OH:18]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 193612641,3-O-di-(t-butyldimethylsilyl)-2-O-tetrahydrofuranylglycerol

Product 1

HCID 193612562-O-tetrahydrofuranylglycerolYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4.25 g (11 mmol) 1,3-O-di-(t-butyldimethylsilyl)-2-O-tetrahydrofuranylglycerol in 30 ml tetrahydrofuran was added 30 ml of tetra-n-butylammonium fluoride (1 mol/l in THF) dropwise and the mixture was stirred at ambient temperature for 2 hours. The reaction mixture was then concentrated and the residue was subjected to column chromatography (silica gel/methylene chloride-methanol) to provide 1.70 g (96%) of 2-O-tetrahydrofuranylglycerol.

Workup

  1. concentrationThe reaction mixture was then concentrated

Sources & evidence

ORD record
ord-301650abbb5949049077a819907e3586
Source dataset
uspto-grants-1998_01
Patent number
US05705188

Reaction notes

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