Imidazole → 3-(tert-Butyldimethylsiloxy)butyric acid methyl ester

HRID 1090326Notes

Reaction equation

HRID 1090326 reaction equation
[OH:1][CH:2]([CH3:8])[CH2:3][C:4]([O:6][CH3:7])=[O:5].N1C=CN=C1.[Si:14](Cl)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]>CN(C=O)C>[Si:14]([O:1][CH:2]([CH3:8])[CH2:3][C:4]([O:6][CH3:7])=[O:5])([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 15146Methyl 3-hydroxybutyrateHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 137127793-(tert-Butyldimethylsiloxy)butyric acid methyl esterYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5.91 Grams (50 mmol) of methyl 3-hydroxybutyrate and 3.74 g (55 mmol) of imidazole were dissolved in 20 ml of DMF and thereto 8.29 g (55 mmol) of t-butyldimethylsilylchloride was added in several portions. After stirring the mixture at room temperature for 30 minutes, ice water was added and extraction with diethyl ether was conducted three times. The extract was washed with a saturated solution of NaCl, dried with anhydrous magnesium sulfate and concentrated under reduced pressure. The concentrate was distilled (62° to 68° C./5 mmHg) to give 10.51 g of methyl (-)-3-t-butyldimethylsilyloxybutyrate (yield: 91%).

Workup

  1. extractionextraction with diethyl ether
  2. washThe extract was washed with a saturated solution of NaCl
  3. dry with materialdried with anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. distillationThe concentrate was distilled (62° to 68° C./5 mmHg)

Sources & evidence

ORD record
ord-f7f7f5c7be3f412ebde8b808fdf00c0f
Source dataset
uspto-grants-1992_01
Patent number
US05081238

Reaction notes

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