Water → HCID 68684710, compound

HRID 2238655Notes

Reaction equation

HRID 2238655 reaction equation
[Si:1]([O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25](=[O:27])[CH3:26])=[CH:21][CH:20]=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.[BH4-].[Na+].O>CO.O1CCCC1>[Si:1]([O:18][C:19]1[CH:24]=[CH:23][C:22]([CH:25]([OH:27])[CH3:26])=[CH:21][CH:20]=1)([C:14]([CH3:16])([CH3:17])[CH3:15])([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 4311764Sodium borohydrideHCID 59659897HCID 59659897, compound

Product 1

HCID 68684710HCID 68684710, compoundYield 99.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

5 g of the 1-(4-{[t-butyl(diphenyl)silyl]oxy}phenyl)-1-ethanone [79-1] was dissolved in a mixture solvent of 50 mL of methanol and 30 mL of tetrahydrofuran, 606 mg of sodium borohydride was added thereto, and stirred at room temperature for 3 hours. The reaction mixture was added with 30 mL of water, and concentrated under reduced pressure. The residue was added with 150 mL of ethyl acetate, washed with water and saturated brine in the subsequent order, and the obtained organic layer was dried over anhydrous magnesium sulfate. The insolubles were filtered, the filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography, to obtain 5.02 g of 1-(4-{[t-butyl(diphenyl)silyl]oxy}phenyl)-1-ethanol [79-2] as a colorless oily product.

Workup

  1. additionwas added
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue was added with 150 mL of ethyl acetate
  4. washwashed with water and saturated brine in the subsequent order
  5. dry with materialthe obtained organic layer was dried over anhydrous magnesium sulfate
  6. filtrationThe insolubles were filtered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-38bf6bbed5d044fba61c2ec3740a674f
Source dataset
uspto-grants-2010_05
Patent number
US07718801B2

Reaction notes

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