Imidazole → Methyl (2S)-2-[(tert-butyldimethylsilyl)oxy]propanoate

HRID 708863Notes

Reaction equation

HRID 708863 reaction equation
[OH:1][C@@H:2]([CH3:7])[C:3]([O:5][CH3:6])=[O:4].N1C=CN=C1.[Si:13](Cl)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]>CN(C=O)C>[Si:13]([O:1][C@@H:2]([CH3:7])[C:3]([O:5][CH3:6])=[O:4])([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 94386methyl (S)-lactate

Product 1

HCID 11053144Methyl (2S)-2-[(tert-butyldimethylsilyl)oxy]propanoateYield 82.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (S)-methyl 2-hydroxypropanoate (1.00 g, 9.61 mmol) in DMF (10 mL) at rt, were added imidazole (0.981 g, 14.41 mmol) and TBS-Cl (1.737 g, 11.53 mmol). The mixture was stirred at rt for 3 h. The reaction mixture was diluted with hexanes. The organic phase was washed with water (2×) and brine, dried (Na2SO4) and concentrated. The crude product was purified by flash chromatography (0 to 10% ethyl acetate/hexanes) to give 17A (1.73 g, 7.92 mmol, 82% yield) as a colorless oil. 1H NMR (400 MHz, chloroform-d) δ ppm 4.34 (q, J=6.7 Hz, 1H) 3.72 (s, 3H) 1.40 (d, J=6.8 Hz, 3H) 0.90 (s, 8H) 0.09 (d, J=10.8 Hz, 6H).

Workup

  1. washThe organic phase was washed with water (2×) and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe crude product was purified by flash chromatography (0 to 10% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-1f0c99352285465fb9989acf947d1882
Source dataset
uspto-grants-2015_11
Patent number
US09174974B2

Reaction notes

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