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Imidazole → [(R)-2-Bromo-1-(2,2-dimethyl-4H-benzo[1,3]dioxin-6-yl)ethoxy]-tert-butyldimethylsilane

HRID 724578
Notes
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Reaction equation

HRID 724578 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 25098927(R)-2-Bromo-1-(2,2-dimethyl4H-benzo[1,3]dioxin-6-yl)ethanol

Product 1

HCID 66810892[(R)-2-Bromo-1-(2,2-dimethyl-4H-benzo[1,3]dioxin-6-yl)ethoxy]-tert-butyldimethylsilane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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

  1. customThe reaction mixture was then partitioned between 200 mL of saturated sodium chloride and 200 mL of diethyl ether
  2. extractionThe aqueous layer was extracted with 200 mL of diethyl ether
  3. washwashed with saturated sodium chloride (3×100 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe product was purified by silica gel chromatography
  7. washeluting with hexanes
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-467a5e2fa25b454e97e412aec84b8286
Source dataset
uspto-grants-2006_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07141671B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes