Imidazole → (S)-5-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-one

HRID 1807057Notes

Reaction equation

HRID 1807057 reaction equation
[OH:1][CH2:2][CH2:3][C@@H:4]1[O:8][C:7]([CH3:10])([CH3:9])[O:6][C:5]1=[O:11].N1C=CN=C1.[C:17]([Si:21]([CH3:24])([CH3:23])Cl)([CH3:20])([CH3:19])[CH3:18].O>CN(C)C=O>[C:17]([Si:21]([CH3:24])([CH3:23])[O:1][CH2:2][CH2:3][C@@H:4]1[O:8][C:7]([CH3:9])([CH3:10])[O:6][C:5]1=[O:11])([CH3:20])([CH3:19])[CH3:18]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 10975778(S)-5-(2-Hydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-one

Product 1

HCID 67299740(S)-5-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-oneYield 74.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Step C A mixture of (S)-5-(2-hydroxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-one (6.8 g, 42 mmol) and imidazole (7.5 g, 107 mmol) in dimethylformamide (40 mL) was added tert-butyldimethylchlorosilane (7 g, 45 mmol). The reaction mixture was stirred at room temperature for 18 h. Water was added. The organic layer was separated, the aqueous layer was then extracted with ethyl acetate twice. The combined organic layers were washed with brine, dried over MgSO4, concentrated to give (S)-5-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-one as a colorless oil (8.6 g, 74%).

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was then extracted with ethyl acetate twice
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8bb2a73c3e3a45e2984b3c70d9b8a85f
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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