Imidazole → (2S)-3-[[(1,1-Dimethylethyl)diphenylsilyl]oxy]-2-methylpropanoic Acid Methyl Ester

HRID 2216987Notes

Reaction equation

HRID 2216987 reaction equation
[OH:1][CH2:2][C@H:3]([CH3:8])[C:4]([O:6][CH3:7])=[O:5].N1C=CN=C1.[Si:14](Cl)([C:27]([CH3:30])([CH3:29])[CH3:28])([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>ClCCl>[C:27]([Si:14]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[O:1][CH2:2][C@H:3]([CH3:8])[C:4]([O:6][CH3:7])=[O:5])([CH3:30])([CH3:28])[CH3:29]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 10192563methyl (2S)-3-hydroxy-2-methylpropanoate

Product 1

HCID 11302759(2S)-3-[[(1,1-Dimethylethyl)diphenylsilyl]oxy]-2-methylpropanoic Acid Methyl Ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methyl (S)-(+)-3-hydroxy-2-methylpropionate (1.06 g; 8.99 mmol) (Aldrich) was dissolved in dichloromethane (10 mL, dried over molecular sieves). Imidazole (0.85 g; 12.41 mmol) (Aldrich) and tert-butyl-diphenylsilyl chloride (2.30 mL; 8.85 mmol) (Aldrich) were added and the mixture was stirred at ambient temperature for 3 hours. The reaction was diluted with additional dichloromethane, washed with water and brine, dried over anhydrous sodium sulfate, filtered, and concentrated to yield methyl (S)-(+)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-propionate as an oil. (Yield 3.17 g; 98.8%).

Workup

  1. washwashed with water and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-374eea85f0b14737976344be38fea772
Source dataset
uspto-grants-2006_09
Patent number
US07112676B2

Reaction notes

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