Imidazole → 3-(tert-butyldimethylsilyloxy)dihydrofuran-2(3H)-one

HRID 1917501Notes

Reaction equation

HRID 1917501 reaction equation
[OH:1][CH:2]1[CH2:6][CH2:5][O:4][C:3]1=[O:7].N1C=CN=C1.[Si:13](Cl)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]>CN(C=O)C.C(OCC)C>[Si:13]([O:1][CH:2]1[CH2:6][CH2:5][O:4][C:3]1=[O:7])([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 545831alpha-Hydroxy-gamma-butyrolactone

Product 1

HCID 50462413-(tert-butyldimethylsilyloxy)dihydrofuran-2(3H)-oneYield 100%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-hydroxydihydrofuran-2(3H)-one (5 g, 49 mmol) in anhydrous DMF (50 mL) was added imidazole (6.7 g, 98 mmol) and TBDMS chloride (8.1 g, 54 mmol). The reaction was allowed to stir under an N2 atmosphere at room temperature overnight. The reaction was diluted with diethyl ether and washed with 1 N aqueous HCl×2 then brine×1. The organic phase was dried over Na2SO4 and the solvent removed in vacuo to yield 3-(tert-butyldimethylsilyloxy)dihydrofuran-2(3H)-one (11 g, 49 mmol) as a clear oil. [M+H] calc'd for C10H20O3Si, 217; found, 217.

Workup

  1. washwashed with 1 N aqueous HCl×2
  2. dry with materialThe organic phase was dried over Na2SO4
  3. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-02697db7b176448ab0ff158d97ad98d0
Source dataset
uspto-grants-2013_12
Patent number
US08618290B2

Reaction notes

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