Imidazole → HCID 131737096, compound

HRID 60694Notes

Reaction equation

HRID 60694 reaction equation
[CH3:1][C:2]1([CH3:14])[O:6][C@H:5]2[O:7][C@H:8]([CH:10]([OH:13])[CH2:11][CH3:12])[CH2:9][C@H:4]2[O:3]1.N1C=CN=C1.[C:20]([Si:24](Cl)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([CH3:23])([CH3:22])[CH3:21].CCOC(C)=O>CN(C=O)C>[CH3:14][C:2]1([CH3:1])[O:6][C@H:5]2[O:7][C@H:8]([CH:10]([O:13][Si:24]([C:20]([CH3:23])([CH3:22])[CH3:21])([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:11][CH3:12])[CH2:9][C@H:4]2[O:3]1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 8857Ethyl AcetateHCID 94078tert-ButyldiphenylchlorosilaneHCID 121396357HCID 121396357, compound2×

Product 1

HCID 131737096HCID 131737096, compoundYield 81.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]propan-1-ol (compound 1e, 2.02 g, 10 mmol) in DMF (30 mL) was added imidazole (6.5 g, 100 mmol) and tert-butylchlorodiphenylsilane (8.22 g, 30 mmol) with stirring. After being stirred at room temperature for 2 hours, the resulting solution was diluted by EtOAc (200 mL), washed with water, brine and dried over Na2SO4. The organic layer was concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluting with 1:10 EtOAc in petroleum ether) to afford 3.6 g of 1-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]propoxy-tert-butyl-diphenyl-silane (compound 3a).

Workup

  1. stirringAfter being stirred at room temperature for 2 hours
  2. washwashed with water, brine
  3. dry with materialdried over Na2SO4
  4. concentrationThe organic layer was concentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel (eluting with 1:10 EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-b4ef72517c3c4141ad3e9fe72baaae22
Source dataset
uspto-grants-2016_09
Patent number
US09441008B2

Reaction notes

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