3,4-dihydro-2H-pyran → Tert-butyldimethyl[2-phenyl-2-(tetrahydropyran-2-yl-oxy)ethoxy]silane

HRID 1468758Notes

Reaction equation

HRID 1468758 reaction equation
[Si:1]([O:8][CH2:9][CH:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[OH:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[O:18]1[CH:23]=[CH:22][CH2:21][CH2:20][CH2:19]1>ClCCl.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:4]([Si:1]([CH3:3])([CH3:2])[O:8][CH2:9][CH:10]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[O:11][CH:19]1[CH2:20][CH2:21][CH2:22][CH2:23][O:18]1)([CH3:7])([CH3:6])[CH3:5]

Participants

5

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 113911162-(Tert-butyldimethylsilyl)oxy-1-phenylethanol

Product 1

HCID 11313702Tert-butyldimethyl[2-phenyl-2-(tetrahydropyran-2-yl-oxy)ethoxy]silaneYield 100%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(tert-butyldimethylsilanyloxy)-1-phenylethanol (0.73 g, 2.9 mmol) and 3,4-dihydro-2H pyran (486 mg, 5.78 mmol) in dichloromethane (30 ml) was added p-toluenesulfonic acid monohydrate (50 mg). The mixture was stirred at room temperature for 12 hours and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent; hexane/ethyl acetate=3/1) to give tert-butyldimethyl[2-phenyl-2-(tetrahydropyran-2-yl-oxy)ethoxy]silane (0.86 g, 2.9 mmol, >99%) as a colorless oil.

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. customThe residue was purified by silica gel column chromatography (eluent; hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-ca0a5801fbc64870be3c71db7fdad13f
Source dataset
uspto-grants-2015_04
Patent number
US09006232B2

Reaction notes

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