Imidazole → HCID 10991787, compound

HRID 60764Notes

Reaction equation

HRID 60764 reaction equation
[OH:1][CH2:2][C@@H:3]1[CH:7]=[CH:6][C:5](=[O:8])[O:4]1.N1C=CN=C1.[C:14]([Si:18](Cl)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([CH3:17])([CH3:16])[CH3:15]>C(Cl)Cl>[Si:18]([O:1][CH2:2][C@@H:3]1[CH:7]=[CH:6][C:5](=[O:8])[O:4]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 10176122(S)-(-)-5-Hydroxymethyl-2(5H)-furanone2×

Product 1

HCID 10991787HCID 10991787, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2.25 g of (25)-2-(hydroxymethyl)-2H-furan-5-one (compound 40b, 2.11 g, 16.0 mmol) and imidazole (1.63 g, 24.0 mmol) in DCM was added tert-butyl(chloro)diphenylsilane (5.2 mL, 20.0 mmol) dropwise. The resulting mixture was stirred at room temperature for 2 hours. The resulting mixture was washed with brine. The aqueous layer was extracted with DCM. The organic layers were combined, washed with 1N hydrochloric acid, dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluting with 0-30% EtOAc in petroleum ether) to afford 4.6 g of (25)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-2H-furan-5-one (compound 40c) as a white solid. MS obsd. (ESI+) [(M+H)+]: 353.

Workup

  1. washThe resulting mixture was washed with brine
  2. extractionThe aqueous layer was extracted with DCM
  3. washwashed with 1N hydrochloric acid
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on silica gel (eluting with 0-30% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-6d003c75252749dea05fc17160195613
Source dataset
uspto-grants-2016_09
Patent number
US09441008B2

Reaction notes

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