Hydrogen Peroxide → HCID 131724568, compound

HRID 1837427Notes

Reaction equation

HRID 1837427 reaction equation
ClB.CSC.[CH3:6][SiH:7]([CH2:9][CH2:10][Si:11]([CH3:21])([CH3:20])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH:18]=[CH2:19])[CH3:8].[OH:22]O>C1COCC1>[CH3:6][SiH:7]([CH2:9][CH2:10][Si:11]([CH3:21])([CH3:20])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][OH:22])[CH3:8]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 131724569HCID 131724569, compoundHCID 178419200HCID 178419200, compound

Product 1

HCID 131724568HCID 131724568, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Monochloroborane-methyl sulfide (1.10 ml, 1.16 g, 10.5 mmol) was added dropwise to a stirred, cooled (0° C.) solution of compound 9 (2.56 g, 10.0 mmol) in THF (30 ml). The reaction mixture was stirred at 0° C. for 24 h, and a solution of hydrogen peroxide (10 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 (MgS04) 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. customdried (MgS04)
  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-f1ddfad65a8440ba925054a0079cf581
Source dataset
uspto-grants-2004_08
Patent number
US06783812B2

Reaction notes

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