Imidazole → [(R)-2-Bromo-1-(2,2-dimethyl-4H-benzo[1,3]dioxin-6-yl)ethoxy]-tert-butyldimethylsilane
Reaction equation
[Br:1][CH2:2][C@@H:3]([C:5]1[CH:6]=[CH:7][C:8]2[O:13][C:12]([CH3:15])([CH3:14])[O:11][CH2:10][C:9]=2[CH:16]=1)[OH:4].N1C=CN=C1.[Si:22](Cl)([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23]>CN(C=O)C>[Br:1][CH2:2][C@@H:3]([C:5]1[CH:6]=[CH:7][C:8]2[O:13][C:12]([CH3:14])([CH3:15])[O:11][CH2:10][C:9]=2[CH:16]=1)[O:4][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To the product of step (d) (10 g, 34.8 mmol) and imidazole (4.7 g, 69.7 mmol) dissolved in 100 mL DMF was added tert-butyldimethylsilyl chloride (5.78 g, 38.3 mmol). The reaction mixture was stirred for 18 hours. The reaction mixture was then partitioned between 200 mL of saturated sodium chloride and 200 mL of diethyl ether. The aqueous layer was extracted with 200 mL of diethyl ether. The organic layers were then combined, washed with saturated sodium chloride (3×100 mL), dried over MgSO4 and concentrated. The product was purified by silica gel chromatography, eluting with hexanes followed by 5% ethyl acetate in hexanes. The desired fractions were combined and concentrated to give the title compound as an oil.
Workup
- customThe reaction mixture was then partitioned between 200 mL of saturated sodium chloride and 200 mL of diethyl ether
- extractionThe aqueous layer was extracted with 200 mL of diethyl ether
- washwashed with saturated sodium chloride (3×100 mL)
- dry with materialdried over MgSO4
- concentrationconcentrated
- customThe product was purified by silica gel chromatography
- washeluting with hexanes
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-f8fe9a395ec648e2b217c62f457c1aab
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08618131B2
Reaction notes
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