Imidazole → 4-t-Butyl-5-[4-(t-butyldimethylsiloxy)-2-phenylbenzo[d]oxazol-6-yl]-3,3-dimethyl-2,3-dihydrofuran

HRID 324180Notes

Reaction equation

HRID 324180 reaction equation
N1C=CN=C1.[CH3:6][C:7]([Si:10](Cl)([CH3:12])[CH3:11])([CH3:9])[CH3:8].CN(C=O)C.[C:19]([C:23]1[C:24]([CH3:45])([CH3:44])[CH2:25][O:26][C:27]=1[C:28]1[CH:42]=[C:41]([OH:43])[C:31]2[N:32]=[C:33]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[O:34][C:30]=2[CH:29]=1)([CH3:22])([CH3:21])[CH3:20].[Cl-].[Na+]>>[C:19]([C:23]1[C:24]([CH3:45])([CH3:44])[CH2:25][O:26][C:27]=1[C:28]1[CH:42]=[C:41]([O:43][Si:10]([C:7]([CH3:9])([CH3:8])[CH3:6])([CH3:12])[CH3:11])[C:31]2[N:32]=[C:33]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[O:34][C:30]=2[CH:29]=1)([CH3:22])([CH3:20])[CH3:21]

Participants

6

Reactant 5

HCID 795ImidazoleHCID 5234Sodium ChlorideHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 155474404-t-Butyl-5-(4-hydroxy-2-phenylbenzo[d]oxazol-6-yl)-3,3-dimethyl-2,3-dihydrofuran2×

Product 1

HCID 155474414-t-Butyl-5-[4-(t-butyldimethylsiloxy)-2-phenylbenzo[d]oxazol-6-yl]-3,3-dimethyl-2,3-dihydrofuranYield 80.6%

Procedure

In nitrogen atmosphere at a room temperature, adding 43 mg (0.63 mmol) of imidazole and 64 mg (0.42 mmol) of TBDMSCl to 2.0 ml of DMF dissolving 102 mg (0.28 mmol) of 4-t-butyl-5-(4-hydroxy-2-phenylbenzo[d]oxazol-6-yl)-3,3-dimethyl-2,3-dihydrofuran (Compound [63]), the mixture was stirred for 2 hours. The mixture was added to saturated aqueous solution of sodium chloride and extracted with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, then dried with magnesium sulfate anhydride and concentrated. The concentrate was applied to a silica gel column and the elution was carried out with the mixture of hexane and ethyl acetate (hexane:ethyl acetate=7:1) to obtain 108 mg of 4-t-butyl-5-[4-(t-butyldimethylsiloxy)-2-phenylbenzo[d]oxazol-6-yl]-3,3-dimethyl-2,3-dihydrofuran (Compound [65]) as a colorless oil. Yield 80.6%

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous solution of sodium chloride
  3. dry with materialdried with magnesium sulfate anhydride
  4. concentrationconcentrated
  5. washthe elution
  6. additionwas carried out with the mixture of hexane and ethyl acetate (hexane:ethyl acetate=7:1)

Sources & evidence

ORD record
ord-e0cdfddad2fa403096a5c4c3cdd53607
Source dataset
uspto-grants-2001_04
Patent number
US06218135B1

Reaction notes

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