Imidazole → (2R)-1-(benzyloxy)-3-[(triisopropylsilyl)oxy]-2-propanol

HRID 1496907Notes

Reaction equation

HRID 1496907 reaction equation
Cl[Si:2]([CH:9]([CH3:11])[CH3:10])([CH:6]([CH3:8])[CH3:7])[CH:3]([CH3:5])[CH3:4].[CH2:12]([O:19][CH2:20][C@@H:21]([OH:24])[CH2:22][OH:23])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.N1C=CN=C1>CN(C=O)C>[CH2:12]([O:19][CH2:20][C@@H:21]([OH:24])[CH2:22][O:23][Si:2]([CH:9]([CH3:11])[CH3:10])([CH:6]([CH3:8])[CH3:7])[CH:3]([CH3:5])[CH3:4])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 139400Triisopropylsilyl chlorideHCID 69508413-(Benzyloxy)propane-1,2-diol

Product 1

HCID 66707553(2R)-1-(benzyloxy)-3-[(triisopropylsilyl)oxy]-2-propanolYield 78.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Chloro(triisopropyl)silane (12.2 mL, 0.057 mol) was added dropwise at 20° C. to a stirred solution of diol 78 (9.52 g, 0.052 mol) and imidazole (5.33 g, 0.078 mol) in DMF (150 mL) and stirring was continued for 16 h. Most of the DMF was removed under reduced pressure and the residue was partitioned between EtOAc and water. The organic extract was washed well with water, then brine, and was evaporated to give an oil, which was chromatographed on silica. Elution with petroleum ether gave fore fractions, and then further elution with EtOAc/petroleum ether (1:19) gave (2R)-1-(benzyloxy)-3-[(triisopropylsilyl)oxy]-2-propanol (79) (13.80 g, 78%) as a colourless oil: [α]19 −0.78° (c, 8.93, CHCl3); 1H NMR (CDCl3) δ 7.41-7.27 (m, 5H), 4.55 (s, 2H), 3.90-3.84 (m, 1H), 3.79-3.72 (m, 2H), 3.59-3.51 (m, 2H), 2.52 (d, J=5.1 Hz, 1H), 1.13-1.03 (m, 21H). APCI MS m/z 339 [M+H]+.

Workup

  1. customMost of the DMF was removed under reduced pressure
  2. customthe residue was partitioned between EtOAc and water
  3. extractionThe organic extract
  4. washwas washed well with water
  5. custombrine, and was evaporated
  6. customto give an oil, which
  7. customwas chromatographed on silica
  8. washElution with petroleum ether
  9. customgave fore fractions
  10. washfurther elution with EtOAc/petroleum ether (1:19)

Sources & evidence

ORD record
ord-1028d5faab6d4f63a4d0e149d101b6ba
Source dataset
uspto-grants-2015_12
Patent number
US09198913B2

Reaction notes

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