Imidazole → Methyl 3-((tert-butyldiphenylsilyl)oxy)-2,2-dimethylpropanoate

HRID 2285271Notes

Reaction equation

HRID 2285271 reaction equation
[CH3:1][C:2]([CH3:9])([CH2:7][OH:8])[C:3]([O:5][CH3:6])=[O:4].N1C=CN=C1.[C:15]([Si:19]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)Cl)([CH3:18])([CH3:17])[CH3:16]>CN(C=O)C>[CH3:6][O:5][C:3](=[O:4])[C:2]([CH3:9])([CH3:1])[CH2:7][O:8][Si:19]([C:15]([CH3:18])([CH3:17])[CH3:16])([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 84152Methyl 3-hydroxypivalateHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 16067138Methyl 3-((tert-butyldiphenylsilyl)oxy)-2,2-dimethylpropanoateYield 113.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of methyl 2,2-dimethyl-3-hydroxypropionate (5.0 g, 37.8 mmol) in DMF (75 mL) was cooled to 0° C. and treated with imidazole (3.86 g, 56.7 mmol) then tert-butyl diphenylchlorosilane (11.8 mL, 45.4 mmol). The mixture was stirred at RT for 22 h then concentrated in vacuo. The residue was partitioned between EtOAc and water. The phases were separated and the aqueous layer was extracted with EtOAc (×2). The combined organic phase was washed with 10% aqueous citric acid solution, saturated aqueous sodium bicarbonate solution and brine, dried (Na2SO4) and concentrated in vacuo to give the title compound as a golden oil (15.93 g, quant.). LCMS (Method 3): Rt 5.32 min, m/z 393.3 [M+Na+].

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe residue was partitioned between EtOAc and water
  3. customThe phases were separated
  4. extractionthe aqueous layer was extracted with EtOAc (×2)
  5. washThe combined organic phase was washed with 10% aqueous citric acid solution, saturated aqueous sodium bicarbonate solution and brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-762b472f7f58447fa45d5c574de73f70
Source dataset
uspto-grants-2015_09
Patent number
US09145413B2

Reaction notes

Loading…