Imidazole → HCID 11077853, compound

HRID 577492Notes

Reaction equation

HRID 577492 reaction equation
[O:1]1[CH2:3][C@H:2]1[CH2:4][OH:5].N1C=CN=C1.[C:11]([Si:15](Cl)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([CH3:14])([CH3:13])[CH3:12]>ClCCl>[C:11]([Si:15]([O:5][CH2:4][C@@H:2]1[CH2:3][O:1]1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)([CH3:14])([CH3:12])[CH3:13]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 5460455(+)-Glycidol

Product 1

HCID 11077853HCID 11077853, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To an ice-chilled mixture of (2R)-oxiran-2-ylmethanol (2.00 g, 27.0 mmol) and imidazole (3.68 g, 54.0 mmol) in anhydrous dichloromethane (60 mL) was added tert-butyl(chloro)diphenylsilane (8.40 mL, 32.4 mmol) dropwise, causing the formation of a white precipitate. The mixture was stirred at 0° C. for 15 minutes, then the cooling bath removed and stirring continued at room temperature for one hour. Aqueous ammonium chloride solution (2M, 100 mL) was added and the layers separated. The aqueous layer was extracted with dichloromethane (100 mL). The combined organic extracts were dried over sodium sulfate, concentrated, and purified by silica gel chromatography (eluting with a gradient of 0-30% ethyl acetate in heptane), affording tert-butyl[(2S)-oxiran-2-ylmethoxy]diphenylsilane (296h, 8.40 g, 99% yield) as an oil. 1H NMR (400 MHz, CDCl3) δ 7.65-7.76 (m, 4H), 7.36-7.49 (m, 6H), 3.88 (dd, J=11.86, 3.30 Hz, 1H), 3.74 (dd, J=11.80, 4.71 Hz, 1H), 3.10-3.20 (m, 1H), 2.76 (dd, J=5.14, 4.16 Hz, 1H), 2.63 (dd, J=5.14, 2.69 Hz, 1H), 1.09 (s, 9H). MS: 330 [M+1].

Workup

  1. customthe cooling bath removed
  2. stirringstirring
  3. waitcontinued at room temperature for one hour
  4. additionAqueous ammonium chloride solution (2M, 100 mL) was added
  5. customthe layers separated
  6. extractionThe aqueous layer was extracted with dichloromethane (100 mL)
  7. dry with materialThe combined organic extracts were dried over sodium sulfate
  8. concentrationconcentrated
  9. custompurified by silica gel chromatography (
  10. washeluting with a gradient of 0-30% ethyl acetate in heptane),

Sources & evidence

ORD record
ord-3c2ad4fc75e6441997c669108a96c917
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

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