Water → HCID 18008048, compound

HRID 988250Notes

Reaction equation

HRID 988250 reaction equation
[Si:1]([O:18][CH2:19][C:20]1[CH:21]=[C:22]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][OH:32])[CH:23]=[CH:24][CH:25]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(Cl)(Cl)Cl.[OH2:38]>C(#N)C.C(OCC)(=O)C>[Si:1]([O:18][CH2:19][C:20]1[CH:21]=[C:22]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([OH:38])=[O:32])[CH:23]=[CH:24][CH:25]=1)([C:14]([CH3:15])([CH3:16])[CH3:17])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 962WaterHCID 5943Carbon TetrachlorideHCID 18008039HCID 18008039, compound

Product 1

HCID 18008048HCID 18008048, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-[3-(t-Butyldiphenylsilyloxymethyl)-phenyl]-hexanol (5.9 g, 13.2 mmol) in acetonitrile (28 mL) is added CCl4 (28 mL) and water (43 mL). To this mixture is added NaIO4 (11.7 g, 54 mmol) and RuCl3(H2O) (100 mg, 0.5 mmol). The resulting mixture is stirred for 2 h then diluted with ethyl acetate, washed with water and brine, dried over MgSO4 and activated charcoal, filtered through celite and concentrated. The residue is purified by flash chromatography (silica, 20% ethyl acetate/5% dichloromethane in hexanes) to give the title compound (3.46 g) as an oil. MS (ESI) 461 (M+H)+.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over MgSO4 and activated charcoal
  3. filtrationfiltered through celite
  4. concentrationconcentrated
  5. customThe residue is purified by flash chromatography (silica, 20% ethyl acetate/5% dichloromethane in hexanes)

Sources & evidence

ORD record
ord-afe608d2e10c4c3c8584efc4e729efb0
Source dataset
uspto-grants-2003_10
Patent number
US06635655B1

Reaction notes

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