Iodine → HCID 69064193, compound

HRID 1785435Notes

Reaction equation

HRID 1785435 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8].[Mg].II.[CH2:20]1[O:23][C@@H:21]1[CH3:22].[Cl-].[NH4+].[OH-].[NH4+]>O1CCCC1.[Cu]I.[Cu]>[Si:7]([O:6][CH2:5][C:4]1[CH:3]=[C:2]([CH2:20][CH:21]([OH:23])[CH3:22])[CH:16]=[CH:15][CH:14]=1)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8]

Participants

10

Reactant 6

HCID 807IodineHCID 14923Ammonium HydroxideHCID 25517Ammonium ChlorideHCID 146261(R)-1,2-EpoxypropaneHCID 5462224MagnesiumHCID 220331471-Bromo-3-((((1,1-dimethylethyl)dimethylsilyl)oxy)methyl)benzene

Product 1

HCID 69064193HCID 69064193, compound

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirring solution of (3-bromobenzyloxy)-tert-butyldimethylsilane (7.0 g, 24 mmol) in tetrahydrofuran (100 mL) under an atmosphere of nitrogen was added magnesium turnings (0.73 g, 30 mmol) and a crystal of iodine. The mixture was heated to reflux for 1 h, cooled to 0° C. and copper (I) iodide (4.57 g, 24 mmol) was added. After stirring at 0° C. for 5 min, (R)-(+)-propylene oxide was added and the mixture was stirred for 2 h. A mixture of ammonium chloride and ammonium hydroxide (5:1, 100 mL) was added, the biphasic mixture was stirred vigorously until the copper salts dissolved, and the layers were separated. The aqueous layer was extracted with ethyl acetate, and the organic extracts were dried over magnesium sulfate and purified by flash column chromatography (ethyl acetate/hexanes). 1H NMR (CDCl3) 7.28 (m, 1H), 7.22 (m, 1H), 7.17 (s, 1H), 7.10 (d, 1H) 4.73 (s, 2H), 4.00 (m, 1H), 2.77 (d, 1H), 2.70 (d, 1H), 1.60 (s, 1H), 1.24 (d, 3H), 0.94 (s, 9H), 0.10 (s, 6H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1 h
  3. stirringthe mixture was stirred for 2 h
  4. additionwas added
  5. dissolutiondissolved
  6. customthe layers were separated
  7. extractionThe aqueous layer was extracted with ethyl acetate
  8. dry with materialthe organic extracts were dried over magnesium sulfate
  9. custompurified by flash column chromatography (ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-64cb8344a4f74ecfb861d0bd45cd28af
Source dataset
uspto-grants-2009_03
Patent number
US07504403B2

Reaction notes

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