Hydrogen Peroxide → HCID 59912411, compound

HRID 1837428Notes

Reaction equation

HRID 1837428 reaction equation
ClB.CSC.C[SiH](C[CH2:10][Si:11]([CH3:19])([CH3:18])[CH2:12][CH2:13]CCC=C)C.OO.[CH2:22]1[CH2:26][O:25][CH2:24][CH2:23]1>>[CH3:19][Si:11]([CH3:18])([CH2:10][Si:11]([CH3:18])([CH3:12])[CH3:10])[CH2:12][CH2:13][CH2:24][CH2:23][CH2:22][CH2:26][OH:25]

Participants

5

Reactant 4

HCID 784Hydrogen PeroxideHCID 8028TetrahydrofuranHCID 131724570HCID 131724570, compoundHCID 178419200HCID 178419200, compound

Product 1

HCID 59912411HCID 59912411, compound

Conditions

Temperature
0 °C

Procedure

Monochloroborane-methyl sulfide (2.03 ml, 2.15 g, 19.5 mmol) was added dropwise to a stirred, cooled (0° C.) solution of compound 10 (2.96 g, 13.0 mmol) in THF (20 ml). The reaction mixture was stirred at 0° C. for 24 h, and a solution of hydrogen peroxide (13 ml, 30% in water) added dropwise and the reaction mixture stirred at 0° C. for 4 h, washed with water and the organic layer extracted into hexane/ethyl acetate (3×30 ml, 1:1). The combined extracts were washed with brine, dried (MgSO4) and the solvent removed in vacuo to yield colorless oil. The crude product was purified by column chromatography [silica gel eluted with hexane/ethyl acetate (4:1)] to yield a colorless oil.

Workup

  1. stirringthe reaction mixture stirred at 0° C. for 4 h
  2. washwashed with water
  3. extractionthe organic layer extracted into hexane/ethyl acetate (3×30 ml, 1:1)
  4. washThe combined extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed in vacuo
  7. customto yield colorless oil
  8. customThe crude product was purified by column chromatography [silica gel eluted with hexane/ethyl acetate (4:1)]
  9. customto yield a colorless oil

Sources & evidence

ORD record
ord-6d0fec66a0864bd5a318fac60aa1b151
Source dataset
uspto-grants-2004_08
Patent number
US06783812B2

Reaction notes

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