Imidazole → HCID 67388345, compound

HRID 513256Notes

Reaction equation

HRID 513256 reaction equation
[C:1]([Si:5]([CH3:8])([CH3:7])Cl)([CH3:4])([CH3:3])[CH3:2].[OH:9][C@@H:10]1[C:15](=[O:16])[CH:14]=[CH:13][C@@H:12]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[CH2:11]1.N1C=CN=C1>CN(C)C=O>[Si:5]([O:9][C@@H:10]1[C:15](=[O:16])[CH:14]=[CH:13][C@@H:12]([O:17][CH2:18][C:19]2[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=2)[CH2:11]1)([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 67384356HCID 67384356, compound

Product 1

HCID 67388345HCID 67388345, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

tert-Butyldimethychlorosilane (26 mg, 0.18 mmol, 1.5 equiv) was added to an ice-cooled solution of (4S,6S)-6-hydroxy-4-(4-methoxybenzyloxy)cyclohex-2-enone (29 mg, 0.12 mmol, 1 equiv) and imidazole (24 mg, 0.35 mmol, 3 equiv) in dimethylformamide (0.5 mL). After 45 min, the reaction mixture was partitioned between water (15 mL), saturated aqueous sodium chloride solution (15 mL), and ethyl acetate (20 mL). The layers were separated. The organic layer was washed with water (2×20 mL) and the washed solution was dried over sodium sulfate. The dried solution was filtered and the filtrate was concentrated. The residue was purified by flash-column chromatography to provide 29 mg of the product, (4S,6S)-6-(tert-butyldimethylsilyloxy)-4-(4-methoxybenzyloxy)cyclohex-2-enone, as a colorless oil (87%).

Workup

  1. customthe reaction mixture was partitioned between water (15 mL), saturated aqueous sodium chloride solution (15 mL), and ethyl acetate (20 mL)
  2. customThe layers were separated
  3. washThe organic layer was washed with water (2×20 mL)
  4. dry with materialthe washed solution was dried over sodium sulfate
  5. filtrationThe dried solution was filtered
  6. concentrationthe filtrate was concentrated
  7. customThe residue was purified by flash-column chromatography

Sources & evidence

ORD record
ord-277ab8d6dd864aae8cead0a5009e4e3e
Source dataset
uspto-grants-2015_08
Patent number
US09102697B2

Reaction notes

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